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  • 1991  (4,350)
  • 101
    Electronic Resource
    Electronic Resource
    GEORDNETE EPOXIDNETZWERKE AUS 4-GLYCIDYLPHENYL-4-GLYCIDYL-BENZOAT und 3- BZW. 4-AMINOPHENYL-4-AMINOBENZOAT Herrn Prof. Dr. D. Braun zum 60. Geburtstag gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 185 (1991), S. 33-42 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The introduction of mesogenic groups in main- and sidechains of epoxy thermosets results in an ordered multiphase network with cellular structure, if gelation occurs below the maximal cure temperature Tmax. Tmax is individual for a given combination of monomers. The multiphase network consists of relatively soft anisotropic cell nuclei and hard isotropic cell walls. If gelation occurs above Tmax single phase networks are obtained. The size of the cell nuclei strongly depends on the used monomers and varies up to two orders of magnitude. The multiphase structure was found to have no impact on the tensile elastic modulus.
    Additional Material: 13 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051850104
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  • 102
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    Radikalbildung aus Hydroperoxiden in Gegenwart starker SäurenHerrn Prof. Dr. D. Braun zum 60. Geburtstag gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 185 (1991), S. 43-50 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The polymerisation of styrene and methylacrylate initiated by hydroperoxides is accelerated in the presence of strong acids such as sulfuric acid, p-toluene-sulfonic acid or perchloric acid. By copolymerising styrene and methylmethacrylate and by phenolic type inhibitors the radical nature of the catalytic effect of the acid was proved. Kinetic experiments demonstrated the acid involvement in the starting reaction.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051850105
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  • 103
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    Durch Matrixmodifizierung und Zusatzstoffe zu Polyesterverbunden mit speziellen EigenschaftenHerrn Prof. Dr. D. Braun zum 60. Geburtstag gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 185 (1991), S. 11-21 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: By modification of the resin matrix and by additives unsaturated polyesters result in materials with a large variety of properties. The mechanical values can be tailor-made by chemical modification of the polymer chain or rubber-like additives. Antistatic properties and electrical conductivity can be achieved by addition of carbon black, graphite or metallic fillers. Furthermore the thermal conductivity can be influenced. Other fillers improve the friction and wear behaviour or lead to a significant reduction of weight when microspheres are added. The tailored modification of properties effectively contributes to meet higher security requirements.
    Notes: Ungesättigte Polyester ergeben durch Modifizierung der Harzkomponente oder durch Additive Werkstoffe mit einem breiten Eigenschaftsprofil. Die mechanischen Werte sind durch chemische Modifikation der Polymerkette oder durch kautschukartige Additive gezielt einstellbar. Antistatische Eigenschaften und elektrische Leitfahigkeit lassen sich durch Zugabe von Rußen, Graphit oder metallischen Füllstoffen erreichen. Gleichzeitig kann auch die Wärmeleitfähigkeit beeinflußt werden. Andere Füllstoffe verbessern das Reibungs- und Verschleißverhalten oder können bei Zugabe von Mikrohohlkugeln zu deutlicher Gewichtsverminderung führen. Die gezielte Veränderung der Eigenschaften trägt wesentlich zum Einhalten erhöhter Sicherheitsanforderungen bei.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051850102
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  • 104
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    NEUE VERARBEITUNGSMETHODEN FÜR RIESELFÄHIGE DUROPLASTEHerrn Prof. Dr. D. Braun zum 60. Geburtstag Gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 185 (1991), S. 23-32 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Duroplastische Formmassen werden nach konventionellen Verfahren der Kunststofformgebung wie Formpressen und Spritzgießen bzw. deren Varianten Spritzpressen und Spritzprägen verarbeitet. Wie in anderen Industriezweigen hat auch hier der wachsende Kostendruck zu einer steten Weiterentwicklung dieser Verfahren geführt. Über erfolgreiche Verfahrensverbesserungen zur Reduzierung der Herstellkosten wird im folgenden berichtet.Die Einführung der Spritzgießverarbeitung für Duroplaste in den 60er Jahren bedeutete gegenüber der bis dahin ausschließlich betriebenen Preßverarbeitung einen erheblichen Rationalisierungsschritt. Die Zykluszeiten ließen sich durch das Aufschmelzen der Formmasse in der Plastifiziereinheit sowie durch das Einbringen von Friktionswärme beim Einspritzvorgang erheblich reduzieren. Heute erlebt die Preßverarbeitung eine Renaissance insbesondere dann, wenn es gilt, hochpräzise Formteile mit minimaler Schwindung und geringstem Verzug herzustellen. Durch Rundtischautomaten, Vorplastifiziergeräte und Entnahmegeräte ließen sich die wirtschaftlichen Nachteile der klassischen Preßverarbeitung weitgehend kompensieren.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051850103
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  • 105
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    Dimensions- und Dichteänderung von Polymidformteilen durch WasseraufnahmeHerrn Prof. Dr. D. Braun zum 60. Geburtstag Gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 185 (1991), S. 51-60 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: The crystallization and solidification behaviour of polyamides are influenced by additives such as nucleating agents or fillers. During processing morphological structures are obtained which affect the shrinkage, linear thermal expansion and dimensional changes due to water absorption. By studying the change of volume after water absorption, the dimensional change in length, breadth and thickness are easily understood.
    Notes: Additive in Polyamiden wie Nukleierungsmittel oder Verstärkungsmittel beeinflussen das Kristallisations- und Erstarrungsverhalten. Während der Herstellung von Probekörpern bilden sich morphologische Strukturen, die die Verarbeitungsschwindung, den linearen Ausdehnungskoeffizienten und die Dimensionsänderung während der Wasseraufnahme beeinflussen. Anhand der Volumenänderungen wird der Zusammenhang zwischen der Wasseraufnahme und der Dimensionsänderung in allen drei Raumrichtungen verständlich dargestellt.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051850106
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  • 106
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    Synthesis of macromonomers of poly(2,6-dimethyl-1,4-phenylene oxide)Dedicated to Prof. D. Braun on the occasion of his 60th birthday. (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 185 (1991), S. 75-86 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Poly(2,6-dimethyl-1,4-phenylene oxide) with exactly one functional endgroup was synthesized by oxidative polymerization, halogen substitution polymerization, and by phase transfer catalysis. Reaction with 4-vinylbenzoyl chloride resulted in a quantitative conversion to a macromonomer as shown by GPC and endgroup analysis. The macromonomer is a glassy material with a Tg from 150 to 190°C depending on the molecular weight.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051850108
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  • 107
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    Poly[1-(2-hydroxyethyl) aziridine] as polychelatogen for liquid-phase polymer-based retention (LPR)Dedicated to Prof. Ernst Bayer on the occasion of his 65th birthday (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 193 (1991), S. 195-203 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Die Eigenschaften von Poly[1-(2-hydroxyethyl) aziridin] wurden im Hinblick auf die Komplexbildung für die Metalle Co(II), Zn(II), Ni(II), Cu(II), Cr(III), Fe(III), Cd(II), Pb(II) und Sr(II) in wäßriger Lösung untersucht. Die LPR-Methode beruht auf der Retention von anorganischen Ionen durch lösliche Polymere in einer Membran-Filtrationszelle und nachfolgender Abtrennung der niedermolekularen Anteile vom gebildeten Polymerkomplex. Die Wechselwirkung des hydrophilen Polymeren wurde als Funktion von pH und Filtrationsfaktor bestimmt. Nach dem erhaltenen Wechselwirkungsmuster bildet Cu(II) die stabilsten Komplexe mit dem Polyaziridin innerhalb des pH-Bereiches von 3 bis 7. Bei pH 3 ist es möglich, Cu(II) von allen anderen Metallionen zu trennen. Sr(II) wird im ganzen untersuchten pH-Bereich nur schwach retentiert. Bei pH 7 traten alle Metalle, außer Sr(II), mit dem Polymeren in Wechselwirkung und wurden nahezu quantitativ retentiert.
    Notes: The metal complexing properties of poly[1-(2-hydroxyethyl) aziridine] for the metals Co(II), Zn(II), Ni(II), Cu(II), Cr(III), Fe(III), Cd(II), Pb(II), and Sr(II) in aqueous phase were investigated. The LPR method is based on the retention of inorganic ions by soluble polymers in a membrane filtration cell and subsequent separation of low-molecular species from the polymer complex formed. The metal interaction with the hydrophilic polymer was determined as a function of pH and filtration factor. According to the interaction pattern obtained, Cu(II) forms the most stable complexes with the polyaziridine within the pH range 3 to 7. At pH 3, it is possible to separate Cu(II) from all other metal ions. Sr(II) is only slightly retained at the pH range investigated. At pH 7, all elements, except Sr(II), did interact with the polymer and were almost quantitatively retained.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051930118
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  • 108
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    Synthesis and characterization of new urethane-acrylic polymers (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 1-10 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Eine neue Klasse von Urethan-Acrylat-Monomeren wurde durch Umsetzung von Diisocyanaten wie Toluylendiisocyanat (TDI) und Hexamethylendiisocyanat (HMDI) mit Hydroxyethylmethacrylat oder Hydroxypropylmethacrylat und gesättigten Alkoholen wie Stearylalkohol oder Decanol hergestellt und durch IR- und NMR-Spektroskopie charakterisiert. Durch radikalische Polymerisation dieser Monomeren wurden Acrylatpolymere mit Urethanseitengruppen erhalten, die IR-spektroskopisch, viskosimetrisch und thermisch charakterisiert wurden.Die thermodynamischen Parameter des Polymerabbaus wurden berechnet; ein möglicher Abbaumechanismus wird vorgeschlagen.
    Notes: A new class of urethane-acrylic monomers was synthesized from diisocyanates such as toluylene diisocyanate (TDI) and hexamethylene diisocyanate (HMDI), unsaturated alcohols like hydroxyethyl methacrylate (HEMA), hydroxypropyl methacrylate (HPMA), and saturated alcohols such as stearly alcohol and decanol. The monomers were characterized by IR and NMR spectroscopy. Urethane pendent acrylic polymers, obtained by polymerizing these monomers, were characterized by IR, solubility viscosity, and thermal studies. The thermodynamic parameters for the degradation were calculated and a probable degradation mechanism is proposed.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870101
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  • 109
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    Glass cloth reinforced composites of castor oil based polyurethanes and epoxy resin (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 33-39 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Durch Umsetzung von Rizinusöl mit Toluylen-2,4-diisocyanat, Hexamethylendiisocyanat, Isophorondiisocyanat oder 4,4′-Diphenylmethandiisocyanat wurden Polyurethan-Präpolymere erhalten, die mit einem Epoxidharz aus Bisphenol-F und mit 1,3-Diaminopropan als Härter in Aceton homogen gemischt wurden. Mit diesen Mischungen getränkte Glasfasermatten wurden in einer Presse ausgehärtet; die Lösungsmittelbeständigkeit, elektrische Eigenschaften, Biegefestigkeit, Izod-Schlagfe-stigkeit und Rockwell-Härte der so erhaltenen Laminate wurde bestimmt. Die Abhängigkeit der elektrischen Leitfähigkeit σ von der Temperatur folgt der empirischen Gleichung σ = σ0, exp(-E/2kT).
    Notes: Prepolyurethanes were obtained by reacting the hydroxyl functionality of castor oil with diisocyanates, namely toluene-2,4-diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and 4,4′-diphenylmethane diisocyanate, respectively. Homogeneous mixtures of prepolyurethanes and epoxy resin (prepared from bisphenol F in alkaline medium) were prepared in acetone containing 1,3-propanediamine as curring agent. Glass reinforced laminates were prepared by interacting PU/epoxy resin mixtures on glass cloth through compression moulding. The laminates were characterized by chemical resistance to solvents, flexural strength, izod impact strength, and Rockwell hardness. The variation of electrical conductivity σ with temperature was found to confirm with the empirical relation σ = σ0 exp(-E/2kT).
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870104
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  • 110
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    Synthesis and characterization of some 2,4′-dibenzyldiisocyanate ionic polymers, 7Part 6: T. Buruianǎ, A. Caraculacu, Rev. Roum. Chim., in press.. Photochromic behaviour of ionenes with viologen units (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 51-59 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Durch Menschutkin-Reaktion wurden Polyurethane mit kationischen Viologen-gruppen hergestellt. Die photochromen Eigenschaften dieser Polymeren in einer Poly(vinylalkohol)-Matrix wurden mit UV- und Laserlicht untersucht.
    Notes: The Photochromic properties by UV and laser irradiation of cationic polyurethanes with viologen groups introducted by Menschutkin reaction were studied and poly(vinylalcohol) was used as matrix.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870106
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  • 111
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    Crystallinity of polyethylene measured by density, DSC, and raman spectroscopy. A comparison (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 87-99 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Im Rahmen dieser Arbeit wurden drei verschiedene Meßmethoden für die Bestim-mung der Kristallinität von Polyethylen angewandt. HDPE, LLDPE und LDPE-Pro-ben wurden  -  nach verschiedener Vorbehandlung  -  durch Dichtebestimmung, DSC und Raman-Spektroskopie untersucht. Die mit verschiedenen Methoden gewonnenen Resultate wurden verglichen, und Korrelationen wurden bestimmt.
    Notes: In this work three different techniques were used to determine the crystallinity of polyethylene. After different pretreatment HDPE, LLDPE, and LPDE samples were investigated by density measurements, differential scanning calorimetry, and Raman spectroscopy. The results were compared and relationships were estabilished between the values measured by the different methods.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870109
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  • 112
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    Alkylation of poly(n-vinylpyrrolidone-co-vinylamine) with esters of phosphorous acids (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 135-142 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Poly(N-vinylpyrrolidon-co-vinylamin) wurde mit Estern verschiedener Phosphorsäuren (Dimethylphosphit, Methanphosphonsäuredimethylester, Trimethylphosphat und Bis-(2-chlorethyl)-phosphonat methyliert, um physiologisch aktive Polymere zu erhalten. Die alkylierten Produkte wurden mittels IR- und NMR-Spektroskopie sowie Elementaranalyse charakterisiert. Der Alkylierungsumsatz hängt vom verwendeten Alkylierungsmittel ab. Die methylierten phosphorhaltigen Polymeren weisen Herbizidaktivität auf und könnten als Pflanzenwachstumshemmer verwendet werden.
    Notes: Alkylation of amino groups bounded to a polymer chain with esters of phosphorous acids was studied in order to obtain physiologically active polymers. Poly(N-vinyl-pyrrolidone-co-vinylamine) was chosen as a polymer-carrier. The phosphorous acid esters used were dimethyl hydrogen phosphonate, dimethyl methanephosphonate, trimethyl phosphate and bis-(2-chloroethyl)-hydrogen phosphonate. The composition and structure of the isolated final products was proved by IR- and NMR-spectroscopy and elemental analysis. It is established that alkylation takes place to various extents.The obtained alkylated phosphorous-containing polymers exhibit herbicidal activity and could find application as plant growth retardants.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870112
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  • 113
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    Bulk grafting of decyl methacrylate onto poly(vinyl chloride) in the presence of a lead carboxylate stabilizer (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 153-167 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Um die Weichmacherpermanenz in PVC zu verbessern, wurde Decylmethacrylat (DMA) in Gegenwart eines Bleistabilisators (LS) mittels radikalischer Polymerisation auf PVC gepfropft. Die Molekulargewichte und Glastemperaturen der erhaltenen Produkte bestätigten, daß homogene PVC-g-PDMA-Copolymere entstanden waren.
    Notes: In order to improve the permanence of the plasticizer in a poly(vinylchloride) (PVC) compound we have studied the free radical polymerization and grafting of decyl methacrylate (DMA) onto PVC in the presence of a lead stabilizer. The influence of different parameters has been investigated and homogeneous PVC-g-PDMA copolymers have been obtained. Their molecular weights and the glass transition temperatures were consistent with the grafted nature of the copolymers.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870114
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  • 114
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    Zur charakterisierung von polymerfilmen und lichtleitfaserummantelungen aus additionsvernetzendem siliconkautschukHerrn Professor Dr. K. Hummel zum 60. Geburtstag gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 187-205 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: The crosslinking behaviour of addition-crosslinking Wacker SilGel 600 silicone was investigated in the temperature range of 50 to 90°C with respect to its dependence on heating time. Measurements of the swelling of thin polymer films on special paper (Pecozet Z10) allow the observation of the swelling process which reaches the swelling equilibrium within a few minutes, the selection of a suitable swelling agent, and the rapid determination of the temperature dependence of the degree of swelling Q. Aside from Q, the „solubility parameter“ of the polymer network, the rate constants, and the activation energy of the crosslinking process can be obtained. Measurements of the swelling combined with determination of Huggins' interaction parameter additionally provide the possibility of determining the density of crosslinking of the polymer films.On the basis of these investigations, a rapid method for characterizing the sheathing of optical fibres could be developed. The cylindrical polymer films detach from the glass core during swelling in toluene (25°C). After 5 min the degree of swelling of the sheathing can be measured.
    Notes: Das Vernetzungsverhalten des additionsvernetzenden Silicons Wacker SilGel 600 wurde im Bereich von 50 bis 90°C in Abhängigkeit von der Heizzeit untersucht. Quellungsmessungen an dünnen Polymerfilmen auf Spezialpapier (Pecozet Z10) gestatten eine Verfolgung des in wenigen Minuten bis zum Quellungsgleichgewicht ablaufenden Quellprozesses, die Auswahl eines geeigneten Quellmittels und die schnelle Ermittlung der Temperaturabhängigkeit des Quellungsgrades Q. Neben Q sind der „Löslichkeitsparameter“ des Polymernetzwerkes, die Geschwindigkeitskonstanten und die Aktivierungsenergie des Vernetzungsprozesses zugänglich. Bei der Kombination der Quellungsmessungen mit einer Bestimmung des Hugginsschen Wechselwirkungsparameters kann auch die Vernetzungsdichte der Polymerfilme ermittelt werden.Auf der Basis dieser Untersuchungen konnte eine schnelle Methode zur Charakterisierung der Ummantelung von Lichtleitfasern entwickelt werden. Die zylindrischen Polymerfilme lösen sich während der Quellung in Toluol(25°C) vom Glaskern. Nach 5 min kann der Quellungsgrad der Ummantelung bestimmt werden.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870116
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  • 115
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    Synthesis and application of thermosensitive microcapsules containing azo groupsDedicated to Prof. Robert Kerber on the occasion of his 65th birthday (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 187 (1991), S. 207-224 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Die Synthese und die thermischen Eigenschaften von zwei reaktiven, symmetrischen Azomonomeren und Modellverbindungen wurden untersucht, um thermolabile Mikrokapseln mit thermosensitiven Azogruppen herzustellen. Die Zerfallskinetik dieser thermisch und photochemisch instabilen Verbindungen ist von erster Ordnung, vergleichbar mit AIBN.Durch Grenzflächenpolykondensation der Azomonomeren mit Ethylendiamin, 1,6-Hexamethylendiamin oder Diethylentriamin wurden azogruppenhaltige Polyamide und Polyharnstoffe erhalten, aus denen thermosensitive Mikrokapseln hergestellt wurden. Mit optimierten Herstellungsbedingungen wurden in hohen Ausbeuten Mikrokapseln einheitlicher Größe mit guten Thermo-Transfer-Druckeigenschaften erhalten.
    Notes: In view of applying thermolabile microcapsules with azo groups as thermosensitive sites it was necessary to study the preparation and the thermal behaviour of two reactive, symmetrical azo monomer-compounds and model compounds. They are thermally and photochemically instable and the kinetics of their decomposition is of first order, comparable to that of AIBN.Azo group-containing polyamides and polyureas were prepared by interfacial polycondensation reaction from ethylendiamine, 1,6-hexamethylenediamine, diethylenetriamine and azo monomer-compounds.These polymers were used to prepare thermosensitive microcapsules. Favourable conditions were found to obtain microcapsules of uniform size, in a high yield, and with good properties in thermo-transfer-print.
    Additional Material: 15 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1991.051870117
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  • 116
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    Halogenation of polymers by dichlorodifluoromethane (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 188 (1991), S. 27-40 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Die Fluorierung von Polyethylen und Polyvinylalkohol wurde mit Dichlordifluormethan CCl2F2 (Freon 12) unter Verwendung von Cobalt-60 γ-Strahlung bzw. elektrischer Lichtbogenentladung durchgeführt und der Einfluß von Reaktionstemperatur und -zeit, Katalysator, Verdünnung etc. untersucht. Dabei wurde bei Polyethylen sowohl die Fluorierung als auch die gleichzeitige Chlorierung beobachtet, wobei der Anteil an Fluorierung bei elektrischer Lichtbogenentladung gewöhnlich höher war als bei Verwendung von γ-Strahlung; in beiden Fällen war dennoch die Chlorierung deutlich bevorzugt. Bei Polyvinylalkohol konnten noch höhere Fluorierungs-bzw. Chlorierungsgrade ermittelt werden.
    Notes: Fluorination of polyethylene and polyvinyl alcohol was carried out by dichloro-difluoromethane under cobalt-60 gamma radiation and under electric spark discharge. The effect of temperature, reaction time, catalyst, inert diluent etc. was studied. Simultaneous chlorination of the polymer samples was observed along with fluorination. The extent of fluorination under electric spark discharge is usually higher than that under gamma radiation. Again, the extent of chlorination is higher than that of fluorination in both the cases. The extent of fluorination as well as chlorination is the highest in case of polyvinyl alcohol.
    Additional Material: 4 Ill.
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    Studies on cellulose acetate phthalate: Estimation of mark-houwink-kuhn-sakurada constants and viscosity-temperature relationship (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 188 (1991), S. 41-49 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Celluloseacetatphthalat (CAP) mit einem Acetylgehalt von 19,5 Gew.-% und einem Phthalylgehalt von 21,4 Gew.-% wurde hergestellt und durch fraktionierte Fällung in fünf Fraktionen mit gleichmäßig abnehmendem Molekulargewicht aufgetrennt. Die Werte für das zahlenmittlere Molekulargewicht (M̄n) dieser Fraktionen wurden membranosmometrisch in 0,05 N NaHCO3 gemessen; die Werte für die Grenzviskosität ([η]) wurden ebenfalls von allen fünf Fraktionen bei verschiedenen Temperaturen bestimmt. Die Beziehung zwischen [η] und M̄n wurde nach der Mark-Houwink-Kuhn-Sakurada-Gleichung ausgewertet, und aus den dabei erhaltenen Werten für v zeigte sich, daß CAP offensichtlich ein sehr steifes Polymeres ist. Die Temperaturabhängigkeit der Viskosität verdünnter CAP-Lösungen wurde nach der Methode von Moore durch einen Arrhenius-Ausdruck beschrieben. Die Aktivierungsenergie der Durchflußgeschwindigkeit hängt sowohl von der Konzentration als auch vom Molekulargewicht ab; aus dem dabei erhaltenen empirischen Parameter Ke kann ebenfalls auf ein steifes Polymeres geschlossen werden.
    Notes: Cellulose acetate phthalate (CAP) having an acetyl content of 19.5 wt.-% and a phthalyl content of 21.4 wt.-% was prepared and fractionated into five fractions of regularly decreasing molecular weight. The values of the number average molecular weight (M̄n) of these fractions were measured in 0.05 N NaHCO3 by the help of high-speed membrane osmometer. The intrinsic viscosity [η] values for all the fractions of CAP in 0.05 N NaHCO3 were also determined at different temperatures. The Mark-Houwink-Kuhn-Sakurada equation was applied to the obtained results and the [η]-M̄n relationships for CAP have been established. The results of the values of v suggest that CAP is a stiff polymer. The temperature dependence of the viscosity of dilute CAP solutions has been described by an Arrhenius expression according to Moore's treatment. The activation energy of flow was found to depend on both concentration and molecular weight through an empirical parameter (Ke). The Ke value obtained for CAP also indicates that CAP is a rigid polymer.
    Additional Material: 6 Ill.
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    Studies on hydride terminated methylhydro-dimethylsiloxane copolymers (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 188 (1991), S. 63-72 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Methylhydro-dimethylsiloxancopolymere wurden aus den Hydrolysaten von Dichlordimethylsilan mit 10, 20, 30, 50 und 70 Vol.-% Dichlormethylsilan hergestellt. Die Copolymeren wurden IR-, 1H-NMR-spectroskopisch und chemisch charakterisiert und als Härter für ein funktionalisiertes RTV-Siliconmaterial eingesetzt. Die Vulkanisateigenschaften wurden geprüft; die Copolymeren mit hohem Hydridgehalt verbesserten die mechanischen Eigenschaften und die thermische Stabilität der Vulkanisate.
    Notes: Synthesis of hydride terminated methylhydro-dimethylsiloxane copolymers from the hydrolyzates of 10, 20, 30, 50 and 70% vol.-% dichloromethylsilane with dichlorodimethylsilane have been carried out. The copolymers were characterized by IR-and 1H-NMR-spectroscopy and standard chemical analysis. They were used as curatives for a standard vinyl functional room temperature vulcanizing (RTV) silicone material based on addition cure, and the vulcanizate properties have been evaluated. The copolymers with high hydride content gave better mechanical properties and thermal stability to the vulcanizates.
    Additional Material: 7 Ill.
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    Thermal behaviour of TiO2-encapsulating polymers (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 188 (1991), S. 73-84 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Die thermischen Eigenschaften von Polystyrol and Poly(methylmethacrylat) mit verkapseltem und dispergiertem TiO2 wurden verglichen. Die verkapselnden Polymeren zeigen zwei thermische Relaxationsbereiche, deren nach Wunderlich ermittelte Aktivierungsenergien denen von dynamischen Dispersionen ähnlich sind. Es wird vorgeschlagen, daß die Niedertemperaturrelaxation durch lokale Änderungen der Konformation der Makromoleküle hervorgerufen wird, während die Hochtemperaturrelaxation dem normalen Glasübergang einschließlich der Wechselwirkung mit TiO2 vergleichbar ist. Das thermische Verhalten nahe der Zersetzungstemperatur in verschiedenen Atmosphären deutet darauf hin, daß in den verkapselnden Polymeren spezifische Strukturen vorhanden sind, die eine große Menge Sauerstoff adsorbieren können.
    Notes: Comparing the thermal properties of TiO2 encapsulating polystyrene and poly(methyl methacrylate) with those of TiO2 dispersion polymers it was found that the encapsulating polymers have two thermal relaxation regions. The activation energy of those thermal relaxation regions was determined using the Wunderlich method and it was found that the values are similar to the activation energy for the dynamic dispersion. It is suggested that the low-temperature thermal relaxation is caused by the local change of conformation of molecular chains, while the high-temperature thermal relaxation is similar to that of the normal glass transition temperature including the interaction with TiO2. In addition, the thermal behaviour near the degradation point in different atmospheres indicates that the encapsulating polymer has a specific structure for adsorbing a large amount of oxygen.
    Additional Material: 8 Ill.
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    Chemical synthesis of processible electrically conducting poly(3-dodecylthiophene) (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 188 (1991), S. 105-111 
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    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Poly(3-dodecylthiophen) (PDDT) wurde auf chemischem Weg synthetisiert und 1H-NMR-, IR- und UV-spektroskopisch charakterisiert. Das bei Raumtemperatur aufgenommene ESR-Spektrum von PDDT zeigt einen g-Wert von 2.0091 und eine Linienbreite von 6.60 Gauss. Aus der Lösung gegossene und mit Iod dotierte PDDT-Filme hatten eine elektrische Leitfähigkeit von 12 S/cm.
    Notes: The chemical synthesis of poly(3-dodecylthiophene) is reported. The polymer was characterized by 1H-NMR, IR and UV absorption spectroscopic techniques. The room temperature electron spin resonance spectrum yielded a g value of 2.0091 and a linewidth of 6.60 Gauss. The solution cast polymer films after doping with iodine exhibited an electrical conductivity of 12 S/cm.
    Additional Material: 4 Ill.
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    N-bromo-poly(styrene-co-divinylbenzene) sulphonamide metal salts. Synthesis and basic properties (1991)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 188 (1991), S. 85-96 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Zwei Methoden zur Herstellung hochmolekularer poröser “Bromamine” (—SO2NBr-Na+) mit Poly (styrol-co-divinylbenzol)-Matrix wurden untersucht, und zwar (a) die Einwirkung von Hypobromiten auf das die entsprechenden Sulfonamidseitengruppen enthaltende Copolymere, und (b) die Einwirkung von Bromiden auf das entsprechende hochmolekulare “Chloramin”. In beiden Fällen wurden Metallsalze des hochmolekularen “Bromamins” erhalten. Das Natriumsalz wurde mit einer 100-proz. Ausbeute an funktionellen Gruppen erhalten; es enthielt 2.1 mmol · g-1 —SO2NBr-Na+ Gruppen, d. h. 4.2 meq · g-1 aktives Brom. Es wurde auch die Stabilität des Harzes getestet, und zwar im Bereich von 20-100°C sowohl im trockenen Zustand als auch in wäßrigen Medien. Darüber hinaus wurden thermoanalytische Messungen bis 1000°C durchgeführt. Es wurden auch Beispiele für die Anwendung des“Bromamins” als polymeres Reagenz für Bromierungen (Iodierungen), Oxidationen, Wasserdesinfektion und Kationenaustausch gegeben. Dieses sehr reaktive polymere Reagenz kann ohne merklichen Verlust seiner Eigenschaften wiederholt debromiert und bromiert werden.
    Notes: Macromolecular pendant group N-monobromosulphonamide metal salts —SO2NBr-M+ having a macroporous styrene-divinylbenzene matrix structure have been obtained by two methods:(a) by the action of aqueous metal hypobromites on the appropriate macromolecular pendant group sulphonamide, and(b) by the action of an aqueous metal bromide on the appropriate macromolecular N-chlorosulphonamide metal salt.In each case the sodium salt product was obtained with a 100% functional yield and it contained 2.1 mmol.g-1 —SO2NBr-Na+ groups, i. e., 4.2 meq · g-1 of active bromine. The stability of the resin was investigated in the range 20-100°C in the dry state as well as in aqueous media.A thermoanalysis (TG, DTG, and DTA curves) was carried out up to 1000°C and its course was interpreted. The resin has brominating, oxidative, microbiocidic, and ionexchanging properties. It reacts in a reversible way: after the loss of the active bromine, it can be reactivated again.
    Additional Material: 5 Ill.
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    Oligopurine · oligopyrimidine tracts do not have the same conformation as analogous polypurine · polypyrimidines (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 511-518 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The ability of tracts of synthetic oligopurine · oligopyrimidines containing both adenosine and guanosine residues to approach the conformation of analogous polypurine · polypyrimidines has been examined as a function of tract length by CD spectroscopy. Tracts of up to 19 contiguous, alternating dA and dG residues yield CD spectra that are distinctly different from that of the analogous alternating polymer. Thus the structural changes reflected in the unusual CD spectrum of poly[d(AG)] · poly [d(CT)] must require even longer tract lengths. Tracts of contiguous adenosines flanked by guanosine residues were seen to approach the CD spectrum of poly[dA] · poly[dT] quite slowly as a function of tract length, requiring more than 24 contiguous adenosines to give CD spectra similar to the homopolymer. These results lead us to the conclusion that oligopurine tracts in vivo are not well modeled by synthetic polypurine · polypyrimidines with one or two base pair repeating units.
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    Conformations and time-resolved fluorescence of oligomers of (-)-epicatechin with 4β → 8 interflavan bonds (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 537-545 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oligomers of (-)-epicatechin with 4β → 8 interflavan bonds, and as many as five monomer units, have been studied by conformational analysis and time-resolved fluorescence. The conformational analysis yields 2x-1 conformations for each oligomer with x monomer units. There are two conformations accessible at each interflavan bond. These conformations are denoted by + and -. The dominant conformations for the trimer and higher oligomers have an interaction between the phenolic hydroxyl groups on monomers i and i+2. This interaction involves the hydroxyl group at C(5) on monomer i, and either C(13) or C(8) of monomer i+2, depending on whether the conformation of the two intervening interflavan bonds is + + or + -, respectively. Minor contributions to the ensemble for the tetramer and pentamer are made by conformations that contain the sequence of successive interflavan bonds denoted by -+ or --. In -+ the interaction between monomer units i and i + 2 involves an aliphatic hydroxyl with a phenolic hydroxyl, and there are no hydroxyl-hydroxyl interactions between units iand i + 2 in --. The onset of a different decay law for the fluorescence when x increases from 3 to 4 may be associated with the appearance of the -+ and -- conformations as minor constituents in the ensemble.
    Additional Material: 10 Ill.
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    α-Helical small molecular size analogues of neuropeptide Y: Structure-activity relationships (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 613-619 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: C-terminal analogues of neuropeptide Y (NPY) of small molecular size have been synthesized. The influence of chain length, single or multiple amino acid substitution, and segment substitutions on receptor binding, pre- and postsynaptic biological activity, and conformational properties have been investigated. Receptor binding and in vivo assays revealed biological activity for NPY Ac-25-36 that increased with increasing α-helicity. In attempts to stabilize the α-helical content, three independent types of modified NPY Ac-25-36 analogues were synthesized. Strong agonistic activities could be detected in a series of discontinuous analogues, which are constructs of N-terminal parts linked via different spacer molecules to C-terminal segments. One of the most active molecules was NPY 1-4-Aca-25-36 (Aca, ε-aminocaproic acid). For the first time conformational properties of a series of small NPY analogues have been investigated by CD, and correlated with biological activity and receptor binding. A C-terminal dodecapeptide segment of NPY with an amount of 50% substitution to the native C-terminal sequence of NPY was found to exhibit significant receptor binding.
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    Conformational energy minimization by simulated annealing using molecular dynamics: Some improvements to the monitoring procedure (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 663-670 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The possibility of using molecular dynamics techniques as a tool for simulated annealing is tested in the case of the molecule of biological interest N-acetyl, N′-methyl amides of 3(S)-hydroxy, 4(S)-amino 6-methyl heptanoic acid [(3S, 4S)-statine] and of its (3R,4S) diastereomer. The approach is able to reach global minimum in the conformational space in the case of the mentioned molecule. A description of the method is given. The use of fractional fluctuations of the internal potential energy as an indicator able to point out transition from a given minimum region to a deeper one is investigated. The results about the lowest energy conformation of (3S,4S) diastereomer are in fairly good accordance with the results obtained in the case of search within the whole Conformational hyperspace.
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    Assignment of protein nmr spectra in the light of homonuclear 3D spectroscopy: An automatable procedure based on 3D TOCSY-TOCSY and 3D TOCSY-NOESYAbbreviations: 3D: three dimensional; TOCSY: total correlation Spectroscopy; NOESY: nuclear Overhauser effect spectroscopy; e. COSY: exclusive correlation Spectroscopy; z.COSY: z-filtered correlation Spectroscopy. (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 699-712 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Automated assignment of proteins is greatly simplified using data from 3D-nmr spectra. A strategy is presented which makes use of 3D-TOCSY-TOCSY and 3D-TOCSY-NOESY; its potential is demonstrated with the example of the spectra of BPTI.The discussion of the potential of 3D-nmr includes the introduction of a simple graph for the description of the information content of multidimensional nmr spectra.
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    Toward nonpeptidal substance P mimetic analogues: Design, synthesis, and biological activity (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 725-733 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,4-Piperazine and 4-hydroxy proline, two small cyclic polyfunctional systems with defined stereochemistry, were introduced as “molecular scaffolds.” We define a “bioactive topology,” which is a derived putative low-energy conformation obtained through theoretical conformational analysis of substance P. Substitution of these molecular scaffolds by pharmacophors characteristic of the bioactive topology of the C-terminal hexapeptide of substance P resulted in active, partially nonpeptidal substance P mimetic agonists. The study discusses the concepts arid tools used to achieve this structural transformation, and points out the need to address flexibility-rigidity issues in an attempt to maintain sufficient molecular plasticity.
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    The solution structure of the lantibiotic gallidermin (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 803-811 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 21-peptide amide antibiotic gallidermin is a potential therapeutic against acne disease. It belongs to the class of polycyclic lanthionine and α,β-clidehydroamino acids containing polypeptides, which were named “lantibiotics.” The structural gene of the recently elucidated lantibiotic gallidermin encodes a precursor peptide containing Ser, Thr, and Cys residues in the Oterminal prolantibiotic part, and an unusually hydrophilic leader peptide. The ribosomally synthesized pregallidermin is posttranslationally modified and processed to a complex peptide antibiotic with four/sulfide rings and two unsaturated residues.The complete solution structure of gallidermin was determined in triffuoroethanol : water (95 : 5) and dimethylsulfoxide by two-dimensional 1H-nmr at 500 MHz, using a combination of double quantum filtered correlated spectroscopy, homonuclear Hartman-Hahn, and nuclear Overhauser enhancement spectroscopy experiments. Using a total number of 152 distance constraints from NOEs and 14 torsional constraints, derived from coupling constants, we obtained a screwlike solution structure of gallidermin. Restrained molecular dynamics simulations yielded a set of five converging structures with an atomic rms difference of 1.7 Å for the backbone atoms, not dependent on the starting structure. The spatial structure model is in excellent agreement with the amphiphilic and channel-forming properties of gallidermin on membranes and its tryptic cleavage at the exposed site between residues 13 and 14.
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    X-Ray conformational study of hydrazino peptide analogues (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 793-801 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: We have solved the crystal structures of nine pseudo-peptide analogues deriving from the hydrazino analogue of glycine or valine (NβH2-NαH-CαHR-CO2H, R = H or iPr) or proline (NβH2-Nα-CαH-CO2H) and containing the hydrazide (CO-NβH-Nα) or Nβ-Z-aminoamide peptidomimetic link. This study gives access to the average geometry of these two links, to their inter- and intramolecular interaction modes, and to their influence on the conformational properties of the molecules.
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    Condensation of DNA by multivalent cations: Considerations on mechanism (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1471-1481 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: DNA is generally found within viruses and cells in a tightly packaged state, typically occupying only 10-4-10-6 of the volume of the uncondensed DNA wormlike coil. Condensation can be induced in vitro at low salt by the naturally occurring polyamines spermidine3+ and spermine4+, by hexammine cobalt (III), and even by Mg2+ in methanol-water mixtures. These condensates generally have an orderly, toroidal, or rodlike shape and size similar to that of DNA gently lysed from phage heads. It is also striking that the condensate size distribution is independent of DNA molecular length from 400 to 40,000 base pairs (bp), but that shorter DNA molecules (e.g., 150-bp mononucleosomal DNA) cannot condense in this fashion. We have constructed a successive association equilibrium theory to attempt to explain these results, using an equation devised by Tanford for micelle formation. Most of the obvious attractive and repulsive free energy contributions (mixing, bending, hydration, and other nearest-neighbor interactions) are linear in the amount of DNA incorporated, but the net attractive ΔG° grows nonlinearly because of the increasing average number of nearest neighbors of each duplex as the particle grows. In order that the size distribution have a maximum, a quadratic repulsive free energy is also required, arising from the electrostatic self-energy of the incompletely neutralized particles. The net attractive free energy per base pair interaction is tiny, on the order of 10-3 kT. Despite the apparent generally correct order of magnitude of the various free energy terms, the calculated size distribution is smaller and narrower than observed experimentally. It appears that the size distribution of condensed particles is determined kinetically rather than thermodynamically. Very short DNA molecules cannot nucleate stable aggregates because they cannot develop adequate overlap, either internally or intermolecularly. A substantial fraction of rodlike condensates is observed in aqueous solutions only with a rather inefficient condensing agent, permethylated spermidine. This suggests that slow condensation kinetics may be required to overcome the high activation energy of highly distorted DNA bends or kinks at the turning points of rods. Evidence is reviewed that condensation may be associated with localized helix structure distortion provoked by condensing agents.
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    Cyclic retro-inverso dipeptides with two aromatic side chains. I. Synthesis (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1503-1512 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of cyclic retro-inverso dipeptides - 2-[(4-hydroxy)benzyl]-5-benzyl-4,6(1H,2H,3H,5H)-pyrimidinedione (c[mPhe-gTyr]), 2-benzyl-5-[(4-hydroxy)benzyl]-4,6(1H,2H,3H,5H)-pyrimidinedione (c[mTyr-gPhe]), and 2-benzyl-5-amino-5-[(4-hydroxy)benzyl]-4,6(1H,2H,3H,5H)-pyrimidinedione {c[(α-amino)mTyr-gPhe]} - were synthesized in order to define the minimum structural requirements for binding affinity with opiate receptors and biological activity. Although the first two compounds lack a free amine proposed to be necessary for receptor recognition, the c[mPhe-gTyr] and c[mTyr-gPhe] analogues serve as model molecules in conformational studies of the target analogue, c[(α-amino)mTyr-gPhe]. The cis- and trans-c[(α-amino)mTyr-gPhe] contain all the functional groups such as the amine and phenolic groups in the tyrosine, and the aromatic group in the phenylalanine, necessary for opiate activity. In addition, the c[(α-amino)mTyr-gPhe] analogues possess similar geometries to the Tyr-Pro part of morphiceptin (Tyr-Pro-Phe-Pro-NH2) whose high μ-receptor activity is attributed to conformations with the Tyr-Pro amide bond in a cis conformation because the peptide bonds assume a cis conformation. However, both analogues are inactive in the guinea pig ileum and the mouse vas deferens assays. This may result from wrong orientation of the benzyl group of the gPhe residue with respect to the (α-amino)mTyr residue.Conformational studies of these molecules using 1H-nmr spectroscopy and molecular mechanics calculations will be reported in the following paper. Results of conformational analysis should provide information about backbone-side-chain interactions in the retro-inverso peptide chains since all the fundamental structural elements of the retro-inverso peptides are included in these model systems even though the peptide bonds must assume a cis conformation.
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    Conformational energy studies of β-sheets of model silk fibroin peptides. I. Sheets of poly(Ala-Gly) chainsPreliminary results were presented at the 1990 fall meeting of the Materials Research Society, Boston, November 1990. (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1529-1541 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new model structure is proposed for the silk I form of the crystalline domains of Bombyx mori silk fibroin and the corresponding crystal form of poly(L-Ala-Gly). It was deduced from conformational energy computations on stacked sheet structures of poly(L-Ala-Gly). The novel sheet structure contains interstrand hydrogen bonds but is composed of antiparallel polypeptide chains whose conformation differs from that of the antiparallel β-sheets that constitute the silk II structure. The strands of the new sheet have a two-residue repeat, in which the Ala residues adopt a right-handed and the Gly residues a left-handed sheet-like conformation. The computed unit cell is orthorhombic, with cell dimensions a = 8.94 Å, b = 6.46 Å, and c = 11.26 Å. The model accounts for most spacings in the observed fiber x-ray diffraction patterns of silk I and of the silk-I-like form of poly(L-Ala-Gly), and it is consistent with nmr and ir spectroscopic data. As a test of the computations, the well-established β-sheet structure of silk II and the corresponding form of poly(L-Ala-Gly) have been reproduced. The computed energies for the two forms of poly(L-Ala-Gly) indicate that the silk-II-like form is more stable, by about 1.0 kcal/mol per residue. The main difference between the two structures is the orientation of the Ala side chains of neighboring strands in each sheet. In the Pauling-Corey β-sheet and in the silk II form, referred to as an “in-register” structure, the Ala side chains of every strand point to the same side of a sheet. In the silk I structure, referred to as “out-of-register,” the side chains of Ala residues in adjacent strands point to opposite sides of the sheet.
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    Comparison of the conformational dynamics of the (1 → 4)- and (1 → 6)-linked α-D-glucans using 13C-NMR relaxationDedicated to Prof. Bruno H. Zimm on the occasion of his 70th birthday. (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1581-1592 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The conformational dynamics of α- (1 → 4)- and α- (1 → 6)-glucan homooligomers in the nanosecond time domain have been compared by measuring the 13C-nmr longitudinal relaxation times T1 for carbons of the terminal and interior sugar residues. Measurements are reported on monomeric glucose and on oligomers containing up to ten glucose residues at room temperature in aqueous solution at concentrations of 3 and 20 g/dL. The carbons of terminal residues display longer relaxation times than do those of interior residues, presumably as a consequence of a greater degree of conformational mobility of the chain ends. The T1s of the reducing terminal residues of all oligomers are significantly longer than those of the corresponding nonreducing termini, a phenomenon that we associate tentatively with the anomeric equilibrium at the reducing end. Carbons of the reducing terminal residues in the β-anomeric form relax more slowly than their α-anomeric counterparts. At 20 g/dL the mean T1s for carbons of the terminal and interior residues attain asymptotic behavior with increasing chain length at a chain length of about six residues, and carbons of the α- (1 → 4)-linked maltooligomers relax significantly more slowly than those of the corresponding α-(1 → 6)-linked isomaltooligomers. The T1s of both glucan series increase with decreasing concentration. This concentration dependence disappears below 3 g/dL, where the T1s of the two series of homoligomers are no longer distinguishable. This suggests that in dilute aqueous solution at room temperature viscous damping effects predominate over contributions to the T1-sensitive conformational dynamics from structural differences in the glycosidic linkage region. At 3 g/dL the approach to long chain-length asymptotic behavior is more protracted than at 20 g/dL, and the T1s of carbons of interior oligomeric residues appear to match the corresponding high-polymer behavior at a chain length of eight and greater.
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    Masthead (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991) 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
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    URL: http://dx.doi.org/10.1002/bip.360311401
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    The three states of globular proteins: Acid denaturationWe dedicate this to Bruno Zimm on the occasion of his 70th birthday, with great admiration for his work and much appreciation for his thoughtful advice on many occasions. (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1631-1649 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: We describe statistical mechanical theory that aims to predict protein stabilities as a function of temperature, pH, and salt concentration, from the physical properties of the constituent amino acids: (1) the number of nonpolar groups, (2) the chain length, (3) the temperature-dependent free energy of transfer, (4) the pKa's (including those in the native state) and their temperature dependencies. We calculate here the phase diagrams for apomyoglobin and hypothetical variant proteins. The theory captures essential features of protein stability including myoglobin's Tm vs pH as measured by P. L. Privalov [(1979) Advances in Protein Chemistry, Vol. 33, pp. 167-241] and its ionic strength vs pH phase diagram as measured by Y. Goto and A. L. Fink [(1990) Journal of Molecular Biology, Vol. 214, pp. 803-805].The main predictions here are the following: (1) There are three stable states, corresponding to native (N), compact denatured (C), and highly unfolded (U), with transitions between them. (2) In agreement with experiments, the compact denatured state is predicted to have enthalpy closer to U than N because even though there is considerable hydrophobic “clustering” in C, this nevertheless represents a major loss of hydrophobic contacts relative to configurations (N) that have a hydrophobic “core.” (3) C becomes more prominent in the phase diagram with increasing nonpolar content or decreasing chain length, perhaps thus accounting for (a) why lysozyme and α-lactalbumin differ in their denatured states, and (b) why shortened Staph nuclease molecules are compact. (4) Of major importance for protein calorimetry is Privalov's observation that the enthalpy of folding, ΔH (T, pH) is independent of pH. The theory accounts for this through the prediction that the main electrostatic contribution to stability is not enthalpic; the main contribution is the entropy, mainly due to the different distributions of protons and small ions in the native and denatured states.
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    The CD of ligand-DNA systems. I. Poly(dG-dC) B-DNA (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1709-1720 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A systematic theoretical study of the CD of double-stranded poly (dG-dC) and its complexes with small molecules is presented. The intrinsic CD of the polymer and the induced CD of a transition belonging to a molecule bound to DNA are calculated using the matrix method. The calculations show considerable differences between pyrimidine-purine and purine-pyrimidine binding sites, and we find that the induced CD of a groove bound molecule is one order of magnitude stronger than that of an intercalated molecule. The results form a sound basis for interpreting the CD of ligand-DNA systems in terms of molecular geometry, interactions, and spectroscopy.
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    Molecular dynamics simulation of Lewis blood groups and related oligosaccharides (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1737-1746 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Molecular dynamics simulations without explicit inclusion of solvent molecules have been performed to study the motions of Lewisa and Lewisb blood group oligosaccharides, and two blood group A tetrasaccharides having type I and type II core chains. The blood group H trisaccharide has also been studied and compared with the blood group A type II core chain. The potential energy surface developed by Rasmussen and co-workers was used with the molecular mechanics code CHARMM. The lowest energy minima of the component disaccharide fragments were obtained from conformational energy mapping. The lowest energy minima of these disaccharide fragments were used to build the tri- and tetrasaccharides that were further minimized before the actual heating/equilibration and dynamics simulations. The trajectories of the disaccharide fragments, e.g., Fuc α-(1 → 4) GlcNAc, Gal β-(1 → 4) GlcNAc, etc., show transitions among various minima. However, the oligosaccharides were found to be dynamically stable and no transitions to other minimum energy conformations were observed in the time series of the glycosidic dihedral angles even during trajectories as long as 300 ps. The stable conformations of the glycosidic linkages in the oligosaccharides are not necessarily the same as the minimum energy conformation of the corresponding isolated disaccharides. The average fluctuations of the glycosidic angles in the oligosaccharides were well within the range of ±15°. The results of these trajectory calculations were consistent with the relatively rigid single-conformation models derived for these oligosaccharides from 1H-nmr data.
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    The solution conformation of tubulin-β(422-434)-NH2 and its Nac-DATADEQG-NH2 fragment based on nmr (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 449-458 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The solution conformation of tubulin-β(422-434)-NH2 (YQQYQDATADEQG-NH2) and its Nac-DATADEQG-NH2 fragment has been studied by two-dimensional 1H-nmr spectroscopy in CD3OH/H2O (90/10 v/v) at neutral and low pH. The 13 amino acid peptide is a segment of the C-terminal region of tubulin, and is directly involved in the selective binding site with microtubule-associated proteins MAP-2 and the τ protein. Based on correlated spectroscopy, total correlation spectroscopy, and rotating frame nuclear Over-hauser effect spectroscopy experiments, a complete assignment of all proton resonances was achieved, and the conformation of the backbone could be deduced from coupling constants, NH temperature coefficients, and nuclear Overhauser effects. The spectroscopic evidence indicates that the T8-Q12 section of both molecules forms one complete α-helical turn, stabilized by a NH(Q12)-C=O(T8) hydrogen bond. Furthermore, strong pH-dependent backfolding of the E11 side chain to its own NH proton was found. In addition, close proximity between the aromatic side chains of Y1, Y4, and the α-helical part, resulting in some substantial chemical shift changes when comparing the entire 13-mer with the octamer, could be explained in terms of a nonclassical kink in the DATA section. The conformational space is dominated by extended structures and the nonextended conformers are only a minor, yet spectroscopically clearly discernible entity. The presence of the α-helical region at the C-terminus of the 13-mer is important because binding studies of this peptide with MAP-2 indicate that the D10-E11-Q12-G13 fragment is critical for the binding interaction.
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    Effects of proline ring conformation on theoretical π-π* absorption and CD spectra of helical poly(L-proline) forms I and II (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 529-535 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Absorption and CD spectra of the π-π* transition near 200 nm are calculated for helical (Pro)10 forms I and II with a variable proline ring conformation characterized by torsion angle χ2 in the range -60° to 60°. The spectra for poly (Pro) I are not sufficiently sensitive to χ2 to suggest a preferred ring conformation. The spectra for poly (Pro) II are more sensitive to χ2, and suggest preferred ring conformations near either or both of the χ2regions -50 ± 10° and 50 ± 10°.
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    Theoretical CD studies of polypeptide helices: Examination of important electronic and geometric factors (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 569-586 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An improved model for calculating the CD of polypeptides has been developed. Excited state wavefunctions were derived from CNDO/S (complete neglect of differential overlap, spectroscopic) calculations on N-methylacetamide. Four discrete peptide-localized transitions were employed: π0π*(NV1), π+π* (NV2), nπ*, and n′π*. Inclusion of the π+π*transition (λ0 = 140 nm) significantly improves the accuracy of the calculated CD spectra in the 180-250-nm region. Spectra were computed for various helical structures, including right-handed α-, αII-, ω-, π-, 310-, and poly(proline)I-helices, and the left-handed poly(proline)II-helix. Sensitivity to changes in the peptide backbone geometry and chain length are examined. Electronic factors such as ground-state charge distribution, hybridization effects, and basis set deorthogonalization have been investigated. The nonconservative nature of the poly (Pro) I and II CD spectra is reproduced, and the helix band present in earlier exciton calculations on the α-helix has been diminished.
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    A stable antiparallel cytosine-thymine base pair occurring only at the end of a duplex (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1087-1094 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ultraviolet hyperchromicity experiments indicate that in DNA duplex formation, a C-T mismatch is destabilizing in the center of a duplex, but behaves as a stable base pair at the terminus of a duplex. The C-T base pair is thought to contain two hydrogen bonds, but has thermodynamic parameters (ΔH° and ΔG° of dissociation) that are similar to a G-C base pair. AMBER molecular mechanics calculations were performed to study the possible structural properties of DNA duplexes with central and terminal C-T combinations. These calculations also indicate that a central C-T pair destabilizes a duplex, while terminal C-T forms a stable base pair. Hydrogen bonding between cytosine and thymine occurs only in the energy-minimized structures when the helix diameter decreases and the propeller twist angle between the bases increases. These changes are found to occur only at the end of a duplex in the calculations, which may explain the experimental results.
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    A molecular dynamics simulation of polyalanine: An analysis of equilibrium motions and helix-coil transitions (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1115-1134 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An understanding of helix dynamics can aid in interpreting the motions of proteins. The conformational transitions that occur also appear to play a role in protein folding. Structural studies of isolated peptides in solution are just becoming available. However, detailed analysis of the helix-coil transition is still not available and will be difficult to obtain experimentally. For these reasons, we performed a long molecular dynamics simulation of polyalanine at high temperature. Using this approach, we obtain a description of the overall structure and inherent flexibility of the chain as well as a structural picture of the conformational changes that occur. In this way, we can address both equilibrium properties of the peptide and the dynamics and mechanism of the structural transitions. Our results correlate fairly well with the available experimental data and previous simulations aimed at addressing α-helix dynamics. The peptide spends the bulk of its time fluctuating between different conformations with intermediate helix contents. Transitions between highly ordered and highly disordered structures were rare, but they occurred rapidly. Our distribution of conformations favored collapsed states. Hence, our transitions to structures with high helical content were from fluctuating compact structures. The conversion between helix and coil occurred sequentially on a residue-by-residue basis. However, there was local cooperativity; the transition of a residue to the coil state was facilitated after a neighboring group became non-helical. The relevance of our results to protein folding is also discussed.
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    On the mechanism of dielectric relaxation in aqueous DNA solutions (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1171-1180 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The complex dielectric response of calf thymus DNA in aqueous saline solutions has been measured from 1 MHz to 1 GHz. The results are presented in terms of the relaxation of the incremental contributions to the permittivity and conductivity from the condensed counterions surrounding the DNA molecules. Measurements of the low-frequency conductivity of the samples also lends support to the condensed counterion interpretation.
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    The cystine-stabilized α-helix: A common structural motif of ion-channel blocking neurotoxic peptides (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1213-1220 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Neurotoxic peptides from venoms of scorpions and honey bees exhibit a consensus pattern in the two disulfide bridgings related to the sequence portions Cys-X-Cys and Cys-X-X-X-Cys. A revised three-dimensional structure of charybdotoxin, as determined by two-dimensional nmr spectroscopy, confirms that the consensus cystine dislocation generates in all these toxins a common structural element, i.e., the cystine-stabilized α-helical (CSH) motif, which may be correlated with their common ion channel blocking activity.
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    Valinomycin and its interaction with ions in organic solvents, detergents, and lipids studied by Fourier transform IR spectroscopy (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1205-1212 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The structure of valinomycin in a range of organic solvents of varying polarity and in detergent and lipid dispersions has been studied by Fourier transform ir Spectroscopy. In solvents of low polarity such as chloroform, ir spectra of valinomycin are fully consistent with the bracelet structure proposed on the basis of nmr Spectroscopy, showing a single narrow amide I component attributable to the presence of β-turns and a single band arising from nonhydrogen-bonded ester C=O groups. K+ complexation results in a downward shift in the amide I band frequency, indicating an increase in the strength of the amide hydrogen bonds, along with a shift to lower frequencies of the ester C=O absorption due to a reduction in electron density in these bonds upon complexation. Identical results were obtained with NH4+, a finding not previously reported.In solvents of both medium (CHCl3/DMSO 3 : 1) and high (pure DMSO) polarity, we find evidence of significant disruption of the internal hydrogen-bonding network of the peptide and the appearance of a band suggesting the presence of free amide C=O groups. In such solvents, complexation with K+ and NH4+ was not observed.The structure of valinomycin in detergent micelles resembles that in nonpolar organic solvents. However, changes were found in the amide I and ester carbonyl maxima as 2H2O penetrated the micelle which suggest significant interaction between the solvent and peptide. Complexation with K+ was reduced in cationic detergent micelles as a result of a decrease in the effective K+ concentration due to charge repulsion at the micelle surface.In lipid bilayers the structure again appears identical to that found in chloroform. As in detergent micelles, the amide I and ester carbonyl bands exhibit shifts that indicate interactions with solvent. Complexation with both K+ and NH4+ is efficient, producing spectral changes similar to those seen in organic solvents.
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    Premelting thermal fluctuational interbase hydrogen-bond disrupted states of a B-DNA guanine-cytosine base pair: Significance for amino and imino proton exchange (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1273-1281 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Modified self-consistent phonon theory when applied to the DNA double helix indicates the existence of fairly long-lived states in which single interbase H bonds are disrupted. One can then postulate a number of situations in which particular disrupted H bonds can enhance particular proton exchange. In this paper we postulate a number of such partially open states for a B-conformation GC base pair and calculate the probability of each of these states for a B-conformation poly(dG) · poly(dC). We compare these probabilities to those probabilities needed to explain various observed proton exchange rates. We propose that, for a GC base pair in B conformation, there are two amino proton exchangeable states - a cytosine amino proton exchangeable state and a guanine amino proton exchangeable state; both require the disruption of only the corresponding inter base H bond. The imino proton exchange, however, requires the disruption of all three inter base H bonds and this defines a third open state. Our calculated probabilities for a GC base pair in these three states are in fair agreement with available experimental estimates from measurements of amino and imino proton exchange.
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    Conformational correlatives of DNA band compression and bidirectional migration during field inversion gel electrophoresis, detected by quantitative video epifluorescence microscopy (1991)
    New York : Wiley-Blackwell
    Biopolymers 31 (1991), S. 1297-1307 
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    ISSN: 0006-3525
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Individual DNA molecules in the Mb size range were monitored by epifluorescence video microscopy during field inversion gel electrophoresis (FIGE). DNA migrating in an agarose gel gives rise to characteristic V-conformational elements and when doing so exhibits a reduced mobility. When the V-conformational elements per DNA molecule are few, the degree of retardation appears proportional to the number of V's, and since larger DNA species exhibit more V's, to DNA size. For a particular pulse frequency, the proportionality breaks down progressively as the number of V-conformational elements per DNA molecule increases. The loss of proportionality between DNA length and migration rate is being correlated with the macroscopically observed loss of electrophoretic size discrimination known as band compression. For a particular pulsing frequency and size class of DNA, the loss of size discrimination is thought to be due to the different orientations of migration, caused by the asymmetric distribution of V-conformational elements when the number of these elements is moderate. Small and very large DNA by contrast migrate with the direction of the biased field. These events, analyzed by microscopic measurement, are consistent with the known macroscopically observed double-valued mobilities in FIGE.
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    Photochemische Reaktionen von Übergangsmetall-Organyl-Komplexen mit Olefinen, 3. [4 + 5]-Cycloaddition konjugierter Diene an Tricarbonyl(η5-2,4-dimethyl-2,4-pentadienyl)mangan (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 3-12 
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    ISSN: 0009-2940
    Keywords: Manganese-mediated cyclization ; Nine-membered carbocycles ; Manganese complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photochemical Reactions of Transition Metal Organyl Complexes with Olefines, 31). - [4 + 5] Cycloaddition of Conjugated Dienes to Tricarbonyl(η5-2,4-dimethyl-2,4-pentadienyl)manganeseTricarbonyl(η5-2,4-dimethyl-2,4-pentadienyl)manganese [1] reacts photochemically with the acyclic conjugated dienes 1,3-butadiene [A], 2-methyl-1,3-butadiene [B], (E)-1,3-pentadiene (C), (E,E)-2,4-hexadiene (D), 2,4-dimethyl-1,3-pentadiene (E), 2,4-hexadien-1-ol (F), and methyl 2,4-hexadienoate (G) in a formal [4 + 5] cycloaddition to give tricarbonylmanganese complexes with η3:2-2,6-cyclononadien-1-yl ligands (2A-2G). In addition, the reaction of 1 with A yields thermolabile [η3:2:2-1-(3-butene-1,2-diyl)-1,3-dimethyl-2,6-cyclononadiene]dicarbonylmanganese (3A) and E,E and E,Z isomers of [η3-1-(2-butene-1,1-diyl)-1,3-dimethyl-2,6-cyclononadiene]tetracarbonylmanganese (4A, 4A] as byproducts. Similarly, 1 reacts with B to form tetracarbonyl[η3-1-(3-methyl-2-butene-1,1-diyl)-1,3,6-trimethyl1-2,6-cyclononadiene]manganese (4B) in a side reaction. The crystal and molecular structures of tricarbonyl(η3:2-1,3,5,5,7-pentamethyl-2,6-cyclononadien-1-yl]manganese (2E) and of 3A are determined by X-ray structure analyses. In each of the formally octahedral complexes unusual long manganese-carbon bonds are found for one coordinated CC double bond of the hydrocarbon ligands.
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    Derivate des Borols, XVI Bis(borol)nickel-Komplexe2) (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 17-23 
    Details
    ISSN: 0009-2940
    Keywords: (Borole)nickel complexes ; Nucleophilic substitution at boron ; 1H-Borole ; Dihydro-1H-borolediide ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Derivatives of Borole, XVI1), - Bis(borole)nickel Complexes2)The dilithium 1-(dialkylamino)dihydroborolediides Li2[C4H4-BNR2] 2a, b: R = Me, Et) react with NiCl2 · DME to give bis(borole)nickel complexes Ni(C4H4BNR2)2. Nucleophilic substitution reactions are used to produce a large variety of derivatives Ni(C4H4BR)2 1 (e.g. R = H, tBu, F, Cl, Br, I, OH, OMe). Treatment of Ni(C4H4BCl)2 (tg) with LiO(CH2)3OLi in THF produces a polymer and a dinuclear complex (μ-{η5:η5-[(CH2)3(OBC4H4)2]}2Ni2 (3) which crystallizes from CH2Cl2 as solvate 3 · CH2Cl2. The complexes 1g and 3 · CH2Cl2 are characterized by X-ray diffraction work. Barriers to internal ring-ring rotation are measured by variable-temperature NMR spectroscopy. The B - H bond of Ni(C4H4BH)2 (1a) is remarkably inert and does not react with H2O or with carboxylic acids in THF at room temperature. With PhCHO slow formation of the benzyloxy compound Ni(C4H4BOCH2Ph)2 (1 m) is observed at 100°C. For typical complexes such as the phenyl derivative 1e cyclic voltammetry in CH2Cl2 reveals an irreversible oxidation at 1.32 and a quasi-reversible reduction at -1.37 V vs. SCE.
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    Derivate des Borols, XVII {η5-[1-(Diisopropylamino)borol]}metall-Komplexe: Synthesen, Protonierung, interne Rotation (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 25-29 
    Details
    ISSN: 0009-2940
    Keywords: Borole complexes ; {η5-[1-(Diisopropylamino)borole]}metal complexes, internal rotation of, protonation of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Derivatives of Borole, XVII1). - {η5-[1-(Diisopropylamino)borole]}metal Complexes: Syntheses, Protonation, Internal RotationNew complexes M(CO)4L (M = Cr, W), cis-M(CO)2L2 [M = Mo, W (not isolated)], and (COD)NiL have been prepared from the Diels-Alder dimer L2, where L is 1-(diisopropylamino)borole, C4H4BNiPr2. Complexes of L can be protonated at the nitrogen atom to give stable salts such as [Cr(CO)4(LH)]BF4, [Fe(CO)3(LH)]BF4, [(C6Me6)Ru(LH)]BF4, and [CpCo(LH)]BF4; B  -  N bond dissociation is not observed. Barriers to internal rotation have been determined by variable temperature NMR spectroscopy for Cr(CO)4L, (COD)NiL, and NiL2. Three processes have been identified: rotation of the NiPr2 group around the B  -  N bond, gear-mesh rotation of the isopropyl groups around the C  -  N bonds, and rotation of L with respect to the counter ligands.
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    Darstellung von (Perfluoralkyl)halogeno-1,3-diselenetanen aus entsprechenden Selenocarbonylfluoriden und Umsetzungen mit Bortrichlorid sowie Arsenpentafluorid1) (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 51-61 
    Details
    ISSN: 0009-2940
    Keywords: Selenocarbonyl compounds, perfluorinated ; 1,3-Diselenetanes, perhalogenated ; 2-Selenabicyclo[2.2.1]hept-5-enes ; 1,3-Diselenetan-2-ylium hexafluoroarsenates ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation of (Perfluoroalkyl)halogeno-1,3-diselenetanes from the Corresponding Selenocarbonyl Fluorides and Reactions with Boron Trichloride or Arsenic Pentafluoride1)Reactions of Hg(SeRt)2 (Rt = C2F5, C3F7, CF3) with (C2H5)2 All or All3 in octamethylcyclotetrasiloxane produce the unstable perfluoroalkaneselenocarbonyl fluorides 1 [R1 = CF3 (1 a), C2F5 (1 b), CF3Se (1 c)]. These compounds are very reactive and polymerize to rubberlike products. On heating the polymers decompose almost quantitatively to the monomers or dimers. In CFCl3 solution 1 dimerizes at 20°C in sunlight to the corresponding cis/trans-1,3-diselenetanes 2. The structure of 2 b is determined by single crystal X-ray diffraction. Different selenocarbonyl derivatives add to unsymmetrically substituted 1,3-diselenetanes 3. 1 a and 1 b react with cyclopentadiene to form the [4 + 2] cycloaddition products 4a and 4c. Halogen exchange reactions take place between 2a  -  d and BCl3. The cis-isomers react much faster than the trans-isomers to give a mixture of cis-, trans-forms of 5. When 2c,d is treated with BCl3 it is possible to isolate and characterize the pure trans-isomer 2d, which is separated by preparative gas chromatography from 5c,d. Fluorine abstraction with formation of 1,3-diselenetan-2-ylium ions (6a  -  f) are accomplished by reactions of 2 or 3 with AsF5 in SO2.
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    Molecular Structure of Hg[C(COF)=SF2=O]2 (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 87-88 
    Details
    ISSN: 0009-2940
    Keywords: Alkylidenesulfur difluoride oxide ; Carbon-sulfur double bond ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hg[C(COF) = SF2 = O]2 is prepared by the reaction of FCO — CH = SF2 = O with HgF2. This compound represents the third known example of an alkylidenesulfur difluoride oxide. Its molecular structure is the same as that of the most abundant of the three isomers of FCO-CH = SF2 = O. This is assumed to be the result of weak intramolecular Hg… O contacts. With the exception of the fluorine atoms bound to sulfur, all atoms lie approximately in one plane.
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    Asterane, XXII. Synthese eines doppelten Tetraasterans: Nonacyclo[10.8.0.02,11.04,9.04,19.06,17.07,16.09,14.014,19]eicosan (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 103-109 
    Details
    ISSN: 0009-2940
    Keywords: Asteranes ; Cage compounds ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Asteranes, XXII1).  -  Synthesis of a Double Tetraasterane: Nonacyclo[10.8.0.02,11.04,9.04,19.06,17.07,16.09,14.014,19]eicosane1,4,5,8-Tetrahydronaphthalene-2,3-dicarboxylic anhydride (9) is dimerized by UV light in dioxane yielding four isomeric [2 + 2] adducts whose methyl ester derivatives are elucidated spectroscopically. The structures of the major products 14 and 16 have been confirmed by X-ray structure analysis. Degradation of the carboxylic groups of 14 afforded the title compound 5.
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    Darstellung aromatischer Fluor-Verbindungen durch nucleophilen Austausch von Nitro-Gruppen gegen Fluorid (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 157-162 
    Details
    ISSN: 0009-2940
    Keywords: Fluoro compounds, aromatic ; Nitrite exchange by fluoride ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Aromatic Fluoro Compounds by Nucleophilic Exchange of Nitro Groups by FluorideThe synthesis of aromatic fluoro compounds from the respective nitro compounds by nucleophilic substitution of nitrite by fluoride is described. Reasonable yields in case of nonactivated nitro compounds are only obtained if the nitrite formed in the reaction is eliminated by acylation. 1-Fluoro-3-nitrobenzene (2) was obtained from 1,3-dinitrobenzene (1), and 1-fluoro-3,5-dinitrobenzene (9) as well as 1,3-difluoro-5-nitrobenzene (10) from 1,3,5-trinitrobenzene (8) in yields up to 92% by reaction of nitro compounds with potassium fluoride in sulfolane at 180 - 200°C in the presence of phthaloyl dichloride (6); 1,2-difluoro-4-nitrobenzene (12) was formed in 58% yield from 2,4-dinitro-1-fluorobenzene (11) in the presence of pyromellitoyl tetrachloride (13).
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    Synthese und Struktur von Bis[bis(diisopropylamino)phosphino]chalkogeniden (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 13-16 
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    ISSN: 0009-2940
    Keywords: Diphosphines, tetrakis(diisopropylamino) ; Phosphinous anhydrides ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Structure of Bis[bis(diisopropylamino)phosphino]chalcogenidesPhosphorodiamidous chalcogeno-anhydrides [(R2N)2P]2X (R = Me2CH; X = S, Se, Te) (2a-c) have been obtained by insertion of elemental sulfur, selenium, or tellurium into the P-P bond of the corresponding diphosphane (1). The structure of 2a and 2c has been confirmed by an X-ray diffraction.
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    (Perfluoralkyl)(dimethylamino)sulfonium-hexafluoroarsenate (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 31-38 
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    ISSN: 0009-2940
    Keywords: Fluorosulfonium salts, reaction with nucleophiles ; (Perfluoroakyl)(dimethylamino)sulfonium salts, preparation and structures of ; Methoxysulfinyl hexafluoroarsenate, alkylation with ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (Perfluoroalkyl)(dimethylamino)sulfonium HexafluoroarsenatesMeN = S(CF3)2 (5) is alkylated by Me3O⊕ AsF⊖6 to Me2N-S(CF3)⊕2 AsF⊖6 (4). From 5 and MeOSO⊕ AsF⊖6 (6) MeOS(O)-N(Me)S(CF3)⊕2 AsF⊖6 (7) is formed as a relatively stable primary product. Decomposition of 7 gives the expected 4 only in poor yield. Nucleophilic substitution of the sulfur-bonded fluorine in CF3SF⊕2 AsF⊖6 (8) by Me3SiNMe2 yields CF3S(NMe2)⊕2 AsF⊖6 (9). Similarly, (CF3)2CFSF⊕2 AsF⊖6 (10) reacts with dimethyl(trimethylsilyl)amine to give (CF3)2CFS(NMe2)⊕2 AsF⊖6 (11). The structures of 4 and 9 are elucidated by X-ray analyses, and the influence of the substituents on the bonding is discussed.
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    Übergangsmetall-Silyl-Komplexe, 36 Zur Frage von Gold-Gold-Wechselwirkungen bei Ph2P[CH2]1(2) PPh2 verbrückten zweikernigen Gold-Silyl-Komplexen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 63-67 
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    ISSN: 0009-2940
    Keywords: Dinuclear gold complex ; Silyl complex ; Gold-gold interaction ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Transition-Metal Silyl Complexes, 361).  -  On the Question of Gold-Gold Interactions in Ph2P[CH2]t(2)PPh2-Bridged Dinuclear Gold Silyl ComplexesDinuclear silyl gold complexes of the type dppm(AuSiR3)2 (1) or dppe(AuSiR3)2 (2) are prepared by the reaction of dppm-(AuCl)2 or dppe(AuCl)2 with two equivalents of LiSi(aryl)3 or LiSi(SiMe3)3 The complex dppe[AuSi(SiMe3)3]2 (2 c) exhibits crystallographic inversion symmetry, and therefore the distance between both gold atoms is a maximum. In dppm-(AuSiPh3)2 (1b) a gold-gold interaction between both gold atoms is observed [Au  -  Au 316.80(3) pm].
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    Cyclobuten-Ringöffnung: Eine nützliche Reaktion zur Synthese doppelsträngiger Moleküle (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 149-156 
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    ISSN: 0009-2940
    Keywords: Cyclobutene, ring-opening ; Poly Diels-Alder reaction ; Molecules, double-stranded ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyclobutene Ring Opening: A Useful Reaction for the Synthesis of Double-Stranded MoleculesSyntheses and ring-opening reactions of the compounds endo-5a - e and 9a - c, all containing cyclobutene rings, are described. From these experiments it is concluded that compound 9a is a useful AB-type Diels-Alder monomer for the synthesis of well-defined double-stranded molecules. The stereochemistry of the adducts endo-4b and endo-5d is determined by X-ray structure analysis.
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    Zur Reaktion von Dialkylphosphiten mit α-Enonen, I Synthese und Allyl-Umlagerung von (1-Hydroxy-2-alkenyl)- und (1-Hydroxy-2-cycloalkenyl)phosphonsäure-dimethylestern (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 175-184 
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    ISSN: 0009-2940
    Keywords: α-Enones, regioselective 1,2-addition of dimethyl phosphite to ; Allylic rearrangement of dialkyl (1-hydroxy-2-alkenyl)phosphonates ; 1-Alkenylphosphonates, 3-acetyloxy- ; 1-Alkenylphosphonates, 3-hydroxy- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of Dialkyl Phosphites with α-Enones, I. - Synthesis and Allylic Rearrangement of Dimethyl (1-Hydroxy-2-alkenyl)- and (1-Hydroxy-2-cycloalkenyl)phosphonatesVarious β,γ-unsaturated α-hydroxyphosphonates 3 are prepared in good yields by NaOCH3-catalyzed regioselective 1,2-addition of dimethyl phosphite to acyclic and cyclic α-enones at -35°C. On acid-catalyzed acetylation, the allylic α-hydroxyphosphonates 3 (R1, R2 + H) rearrange under thermodynamic control; yielding the new 3-acetyloxy-1-(cyclo)alkenyl derivatives 8, from which the transposed allylic alcohols 11 are readily obtained. Using shorter reaction times, acetylation of compounds 3 affords mixtures of 1- and 3-acetylated products, 10 and 8, respectively.
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    Trioxypentafulvenes, 2 synthesis of 1-substituted 2,3,6-trioxypentafulvenes (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 207-212 
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    ISSN: 0009-2940
    Keywords: 2,3,6-Trioxypentafulvenes ; Keto-enol tautomerism ; Push-pull system ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses of 2,3,6-trioxypentafulvenes with a free position at the ring are described, in which the protection of the C-3 hydroxy group as methoxy or acetoxy derivative has been required. The difference in the behavior of the title compounds in relation to the previously reported 1,4-disubstituted 2,3,6-trihydroxypentafulvenes 2a-e, which only exhibit enol forms, is discussed and attributed to the disappearance of the push-pull system formed by the C-3 enol group and the C-4 electron-withdrawing substituent.
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    Neue O6-Makrocyclen mit 2,2-Bis(2-furyl)propan-Einheiten (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 233-235 
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    ISSN: 0009-2940
    Keywords: Hexaoxacyclotriacontadodecaenes ; Macrocycles ; 2,2-Bis(2-furyl)propane ; 2,5-Bis[1-(2-furyl)-1-methylethyl]furan ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New O6 Macrocycles with 2,2-Bis(2-furyl)propane UnitsThe macrocycles 3a and 6 are prepared in 29 and 16% yield by cyclization of dilithiated 2,2-bis(2-furyl)propane (1) and 2,5-bis[1-(2-furyl) 1-methylethyl]furan (5), respectively, with ethyl N,N-dimethylcarbamate (2).
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    Umlagerungen von 1,4,4- und 2,2,5-Trimethylbicyclo[3.2.1]oct-6-yl-Kationen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 237-240 
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    ISSN: 0009-2940
    Keywords: Bicyclo[3.2.1]oct-6-yl cations ; Wagner-Meerwein rearrangements ; Alkyl-bridged ions ; Conformational effects ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Rearrangements of 1,4,4- and 2,2,5-Trimethylbicyclo[3.2.1]oct-6-yl Cations1,4,4-Trimethylbicyclo[3.2.1]oct-6-yl cations (18) are generated from the tosylhydrazone 7, by nitrous acid deamination of the amines 6 and 8, and by acetolysis of the brosylates 21 and 24. The product distributions are but slightly affected by the configuration (exo vs. endo) of the leaving groups. The predominant product, 1,4,4-trimethylbicyclo[3.2.1]octan-exo-6-ol (11) is formed without significant redistribution of a 6-2H label. The degenerate Wagner-Meerwein rearrangement of the parent bicyclo[3.2.1]oct-6-yl cation is virtually eliminated by the presence of two methyl groups at C-4. Enhanced conformational strain, raising the barrier to ring flipping, accounts for these observations. Minor products (12, 13) arise from a 7,6-hydride shift of 18, followed by Wagner-Meerwein rearrangement. When the 2,2,5-trimethylbicyclo[3.2.1]oct-6-yl cation (19) is generated directly from the tosylhydrazone 17, the tertiary alcohol 13 is obtained as the major product. The conformational barrier to Wagner-Meerwein rearrangement is compensated by the incipient stabilization of the tertiary carbocation 20.
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    Notizen/Notes Synthesis of 1-Phenyl-1,2- and 4-Phenyl-1,5-dihydropentalenes (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 403-405 
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    ISSN: 0009-2940
    Keywords: 1,2-Dihydropentalenes ; 1,5-Dihydropentalenes ; Rearrangements ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An efficient one-pot synthesis of 3-substituted 1-phenyl-1,2-dihydropentalenes from α,β-unsaturated ketones is described. These compounds can be rearranged to their 1,5-dihydro isomers using different methods such as acid catalysis and vacuum-flash thermolysis or by chromatography on alumina.
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    URL: http://dx.doi.org/10.1002/cber.19911240226
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    Electrochemical Investigations on Methylenephosphines and Related Systems (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 417-421 
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    ISSN: 0009-2940
    Keywords: Methylenephosphines ; Voltammetry, cyclic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Electrochemical investigations on a selection of methylenephosphines 1 and related systems are reported. They are shown to possess an irreversible oxidation and reduction wave. An exception is diaminodiphosphene, which reversibly forms a radical anion. A relative ordering of frontier orbitals is possible, based on the redox properties of these systems.
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    Die Kristallstrukturen von Kalium-, Rubidium- und Cäsium-trifluororthocarbonat mit einer Bemerkung zum Bariumsulfat-Typ1 (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 321-327 
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    ISSN: 0009-2940
    Keywords: Trifluororthocarbonates of potassium, rubidium, cesium ; Phase transitions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Crystal Structures of Potassium, Rubidium, and Cesium Trifluororthocarbonate and a Remark Concerning the Barium Sulfate Type1)Crystals of potassium, rubidium, and cesium trifluororthocarbonate (9a, 9b, and 9c) have been grown by Ostwald ripening in CH3CN applying a COF2 pressure of 3 bar. According to X-ray single-crystal structure analysis, 9a, 9b, and 9c belong to the baryte-structure family with an pseudotetrahedral anion being dynamically disordered at room temperature. All of the title compounds undergo a phase transition into a monoclinic, completely ordered low-temperature form, which has been refined for 9c. The C - O bond seems to be shortened by polar interactions. The results obtained with 9a, 9b, and 9c at room temperature indicate that the type of disorder found in 9 might be generally present in baryte-type compounds.
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    Selektivitäten bei Photoadditionen an multifunktionelle Coffein-Derivate (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 339-345 
    Details
    ISSN: 0009-2940
    Keywords: Photoadditions ; Caffeine derivatives ; Calculations, AM1 ; Diradicals ; Propellanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Selectivities in Photoadditions with Multifunctional Caffeine DerivativesElectronically excited stilbene (21*), 4,4′-dichlorostilbene (1*), and 4,4′-dimethoxystilbene (18*) are trapped by caffeine derivatives 2, 13, or 22 with variable results. While 1* and 2 react predominantly at the imino double bond (substitutive and fragmentating additions), 1* or 18* and 13 produce mostly propellanes by [2 + 2] photocycloaddition, which hydrolyze or may be hydrolyzed. 21* and the relatively electron-poor compound 22 produce mostly propellanes, which always show a preponderance of the syn-10, anti-11 stereoisomers. These selectivities as well as the competition with reactions at the imino double bonds are rationalized on the basis of diradical mechanisms with the aid of semiempirical AM1 calculations. Earlier results on closely related transformations are also discussed.
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    Addition von Phosphor-Nucleophilen an Benzothiet (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 377-381 
    Details
    ISSN: 0009-2940
    Keywords: Phosphorus compounds, organic ; Phosphorus heterocycles ; Arbuzov rearrangement ; Mechanism, SN2, SN1 ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Addition Reactions of Phosphorus Nucleophiles to BenzothieteTrialkyl phosphites 4 add to the o-quinoid form 2 of benzothiete (1) to yield the phosphonates 6. An intermolecular migration of an alkyl group from oxygen to sulfur is the most important feature of this transformation. The rearrangement - related to the Arbuzov reaction - can be avoided in a two-step process by the subsequent action of PCl3 and alcohol; thus the phosphonates 10 are generated. Analogous to 2 → 6, dimethyl phenylphosphinate (11) furnishes 13. In contrast, the cyclic esters 14a-d form 2:1 adducts, namely the 12- to 15-membered heterocyclic compounds 17a - d. An intramolecular rearrangement in a 1:1 adduct is only observed for the 1,3,2-dioxaphosphepine 14e, a benzylic system which allows an SN1 process generating the 1,6,2-oxathiaphosphecine 18e. A similar rearrangement at a tertiary carbon center is prevented by the competitive addition of water (1 + 14f → 20).
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    Dispiro-1,2,4-trioxolane durch Ozonolyse von Cycloalkylidencycloalkanen auf Polyethylen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 391-396 
    Details
    ISSN: 0009-2940
    Keywords: Ozonolysis ; Cycloalkylidenecycloalkanes ; Dispiro-1,2,4-trioxolanes ; Thermolysis ; Photolysis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dispiro-1,2,4-trioxolanes by Ozonolysis of Cycloalkylidenecycloalkanes on PolyethyleneOzonolyses of symmetrical (1b - d) and of unsymmetrical cycloalkylidenecycloalkanes (8a, b) afforded the dispiro-1,2,4-trioxolanes 4b - d and 9a, b, respectively. Their thermal decompositions gave mixtures of the cyclic ketones (3) and lactones (6). Photolyses afforded in addition to 3 and 6 the cyclic anhydrides 13, which are isomeric with the corresponding dispiro-1,2,4-trioxolanes.
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    Pseudooxokohlenstoff-Anionen der Semidreiecksäure (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 665-669 
    Details
    ISSN: 0009-2940
    Keywords: Semideltic acid ; Cyclopropenylium cations ; Pseudooxocarbon anions ; Semideltate anions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pseudooxocarbon Anions of Semideltic AcidNovel pseudooxocarbon anions of semideltic acid (2) can easily be obtained by stepwise substitution of the dimethylamino groups of the cyclopropenium perchlorate 8. Treatment of 8 with cyanamide or malononitrile in the presence of triethylamine leads to the triafulvenes 9 and 13. Two cyanoimino groups are successfully introduced into the cyclopropenylium system by treating 9 with excess cyanamide/potassium ethoxide. Under the same conditions malononitrile reacts with 13 to yield the potassium salts 14 and 17. The thioamide 26 of semideltic acid is obtained by treating the triphenylphosphonium salt 24 with H2S/pyridine and subsequent hydrolysis of the intermediate 25. With the anions of cyanamide or malononitrile ring-opening reaction of the cyclopropenylium system of 24 occurs to yield the push-pull phosphonium salts 28 and 29.
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    Kohlenwasserstoffverbrückte Metallkomplexe, XVIII. Heterometallische Ethylen-verbrückte Komplexe (OC)5ReCH2CH2Mn(CO)5, (OC)5ReCH2CH2Ru(CO)2Cp, (OC)5ReCH2CH2Os(CO)4CH2CH2Re(CO)5 und (OC)5ReCH2CH2CH2Os(CO)4Os(CO)4(CO)4Os(CO)4CH2CH2Re(CO)5 (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1059-1063 
    Details
    ISSN: 0009-2940
    Keywords: Ethylene-bridged metal complexes ; Ethanediyl complexes ; Manganese, Rhenium, Ruthenium, Osmium carbonyls ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hydrocarbon-Bridged Metal complexes, XVIII. - Heterometallic Ethylene-Bridged Complexes (OC)5ReCH2CH2Mn(CO)5, (OC)5ReCH2CH2Ru(CO)2Cp, (OC)5ReCH2CH2Os(CO)4CH2CH2Re(CO)5 and (OC)5ReCH2CH2CH2Os(CO)4Os(CO)4(CO)4Os(CO)4CH2CH2Re(CO)5Addition of [(OC)5Re(C2H4)]+ to the carbonylmetallates [Mn(CO)5]-, [RuCp(CO)2]-, [Os(CO)4]2-, [Os3(CO)12]2- affords the title complexes in a directed way. The dynamic behaviour of (OC)5ReCH2CH2Mn(CO)5 in solution is attributed to a dyotropic exchange of the pentacarbonylmetal groups on the CH2CH2 bridge.
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    Arsen(III)-, Antimon(III)- und Bismuth(III)-halogenid-Komplexe des [2.2.2]Paracyclophans: Vom lockeren van-der-Waals-Addukt zu stark gerichteten π-Komplexen mit zwei- und dreifacher externer η6-Koordination (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1089-1093 
    Details
    ISSN: 0009-2940
    Keywords: [2.2.2]Paracyclophane ligand ; (η6)π Complexes ; Arsenic(III) complexes ; Antimony(III) complexes ; Bismuth(III) complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Arsenic(III), Antimony(III), and Bismuth(III) Trihalide Complexes of [2.2.2]Paracyclophane: From Weak van der Waals Coordination to Strongly Directional π Complexation with Single or Double External η6 Coordination[2.2.2]Paracyclophane forms the adducts C24H24·AsCl3 (1), C24H24·(SbCl3)2·1/2 C6H6 (2), and C24H24·(BiCl3)3·C6H6 (3). For solutions in polar solvents NMR spectra indicate extensive dissociation and/or fluxionality. In the crystals adduct 1 features a weak addition of the AsCl3 molecule to one open side of a paracyclophane molecule with long intermolecular contacts approaching C3v symmetry. - Crystalline 2 shows SbCl3 coordination to two of the benzene rings of the hydrocarbon in a quasi-centered η6 mode, while one of the benzene rings remains uncoordinated. Chlorine-bridging between antimony atoms leads to tetrameric units (SbCI3)4 in the lattice. - In the bismuth compound 3 each benzene ring of the hydrocarbon is engaged in centroid (η6)π complexation, with the BiCl3 units crosslinked by chlorine bridges. The average of the Bi-ring distances (3.08,2.98, and 2.99 Å) is shorter than for the Sb-ring distances in 2 (3.047 and 3.050 Å), indicating stronger bonding. The crystal benzene is not coordinating.
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    Intramolecular, Metallacyclic Organoaluminium, -gallium and -indium Addition Compounds Crystal Structure of 1-Galla-5-azabicyclo[3.3.3]undecane (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1113-1119 
    Details
    ISSN: 0009-2940
    Keywords: Metallacyclic organoaluminium, -gallium and -indium compounds ; MOVPE precursors ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Intramolecularly base-stabilized four-coordinated metallacyclic organoaluminium, -gallium, and -indium compounds C5H10-Al(CH2)3NMe2 (4), C4H8Ga(CH2)3NMe2 (5), C5H10Ga(CH2)3N-Me2 (6), C5H10GaCH2CH(Me)CH2NMe2 (7), C4H8Ga(CH2)4NMe2 (8), C5H10Ga(CH2)4NMe2 (9), EtAl[(CH2)3]2NMe (10), MeGa-[(CH2)3]2NMe (11), EtGa[(CH2)3]2NMe (12), MeIn[(CH2)3]2NMe (13), and (14) have been synthesized by the reaction of [3-(dimethylamino)propyl]aluminium dichloride (1), [3-(dimethylamino)propyl]gallium dichloride (2), [3-(dimethylamino)-2-methylpropyl]gallium dichloride (3), or [4-(dimethylamino)butyl)gallium dichloride with the respective bis-Grignard reagents or by the reaction of the organometal dichlorides RMCl2 with bis[3-(chloromagnesio)propyl]methylamine or with N,N′-bis[3-(chloromagnesio)propyl]-N,N′-dimethyl ethylenediamine. Aluminium or gallium trichloride reacts with tris[3-(chloromagnesio)propyl]amine to give Al[(CH2)3]3N (15) and Ga[(CH2)3]3N (16). The 1H-, 13C-NMR and mass spectra of the new compounds as well as the X-ray crystal structure of 16 are discussed. 4, 6, and 12 have been tested successfully as MOVPE precursors.
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    Übergangsmetallkomplexe von Diazenen, XXVII. Eisencarbonyl-induzierte o-Semidin-Umlagerung von 1-Alkyl-2-aryldiazenen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1143-1148 
    Details
    ISSN: 0009-2940
    Keywords: Ironcarbonyl complexes ; ortho-Metallation ; o-Semidine rearrangement ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Iron Carbonyl Induced o-Semidine Rearrangement of 1-Alkyl-2-aryldiazenesIrradiation of pentacarbonyl iron in the presence of Me3C - N=N - Ar (Ar=phenyl, p-tolyl, p-CH3OC6H4) produces in the first step ortho-metallated complexes of the type Me3C - N - N(H)RC6H3Fe(CO)3Fe(CO)3 (2a-c, R=H, Me, MeO). In a thermal consecutive step these intermediates undergo an o-semidine rearrangement to Me3C - NFe(CO)3 - Fe(CO)3N(H)RC6H3 (1a-c). The structure of 1a has been elucidated by X-ray structure analysis. Dynamic 13C-NMR spectra indicate restricted rotation of the Me3C group and hindered carbonyl scrambling for the latter and former complexes, respectively.
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    Heterogeneous Photocatalysis, IX. Zinc Sulfide Catalyzed Photoreduction of Carbon Dioxide (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1161-1162 
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    ISSN: 0009-2940
    Keywords: Semiconductor ; Photocatalysis ; Carbon dioxide ; Formate ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbon dioxide is catalytically reduced to formate in a suspension of zinc sulfide in water/2,5-dihydrofuran when irradiated (λ ≥ 290 nm). Turnover rates are in the range of 1.5 monolayers CO2/h. No reaction occurs at pH=12, and a very slow one at pH=3.2,5-Dihydrofuran functions as reducing agent which is oxidized to dehydro dimers. When it is substituted by 2-propanol, no CO2 reduction is observed. Semiconductor photocatalysis by a two-electron transfer from zinc sulfide to adsorbed hydrogen carbonate is assumed as the key step of CO2 fixation.
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    Cycloadditions, 47. A Route to Functionalized Cyclic Ethers by Intramolecular Cycloadditions of Unsaturated Nitro Ethers (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1181-1186 
    Details
    ISSN: 0009-2940
    Keywords: Stereoselective cyclizations ; Ethers, cyclic ; Dipolar cycloaddition ; Nitro olefins ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A convenient conversion of aldehydes via nitroolefins 2 into cyclic ethers 6 fused to an isoxazoline ring involves formation of unsaturated nitroalkyl ethers 4 and subsequent intramolecular cycloaddition of an in situ-formed nitrile oxide olefin. The cyclization proceeds with stereoselective formation of trans over cis isomers in the tetrahydrofuran series and opposite stereoselectivity in the tetrahydropyran and hexahydrooxepine series, depending on the substituent R in the original nitro compound, thus providing access to stereoselectively functionalized cyclic ethers.
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    Intra- und extraannular funktionalisierte [2.2.2]Phane mit Dreifachbindung: Synthese und Eigenschaften (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1223-1227 
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    ISSN: 0009-2940
    Keywords: Cesium effect ; Clathrate ; Cyclophanes ; Acetylene, diphenyl ; Rigid-group principle ; Tolane ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Intra- and Extraannularly Functionalized [2.2.2]Phanes: Syntheses and PropertiesThe severely strained new cyclophanes 7b-f, consisting of bridged tolane subunits and bearing intraannular substituents R, were prepared mainly to study steric interactions of R with the “π cloud” of the triple bond. These compounds exist in a rigid twisted conformation, whereas the unsubstituted reference compound 7a and the extraannularly functionalized azo compound 9 show C2 symmetry. 9 forms a 1 : 1 clathrate with toluene.
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    Chiral Organometallic Reagents, I Stereoselective Exchange of Diastereotopic Bromine Atoms by Lithium in 1,1-Dibromo-3-(trimethylsilyloxy)alkanes (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1243-1252 
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    ISSN: 0009-2940
    Keywords: Carbenoids ; Bromine-lithium exchange ; Asymmetric induction ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bromine-lithium exchange in 1,1-dibromo-3-(trimethylsilyl-oxy)alkanes 4 and 6 affords the carbenoids 8 and 14, which have been added to ketones, aldehydes, arylboronates, and silylating agents. Diastereoselectivity in the generation and trapping of the carbenoids ranged between 70 - 90% for 8 and 〉90% for 14.
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    4,9,14,19-Tetrafunctionalized Pagodanes de novo Synthesis - Functional Group Manipulations (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1271-1289 
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    ISSN: 0009-2940
    Keywords: Dibenzo compounds, rigid face-to-face ; Photocycloadditions, [6 + 6] Benzo, Benzo ; Pagodanes, 4,9,14,19-tetrafunctionalized ; Functional Group Manipulations ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Various 4,9,14,19-tetrafunctionalized pagodanes are prepared by a de novo route commencing from appropriately substituted isodrin analogues (3, 4). With the 14,19-dimethoxypagodane-4,9-dicarboxylic esters 30/31, isolated after 16 one-pot operations (ca. 40 functional changes) in ca. 6.5% overall yield (ca. 84% per operation, ca. 93% per functional change), the scope for further functional group manipulations on the pagodane sphere is explored (e.g. diketone dicarboxylic ester 35, dimethoxy diketone 37, tetraketone 41). In two face-to-face dibenzo substrates (17, 49), clean photoequilibration with the corresponding syn-o,o'-dibenzo isomers (19, 50) (75: 25 and 80: 20, resp.) is observed upon direct excitation (λ=254 nm).
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    Die Synthese von Chlor(trichlormethyl)sulfin, Cl3C(Cl)C=SO (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1311-1312 
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    ISSN: 0009-2940
    Keywords: Anthracene adducts ; Sulfine, chloro(trichloromethyl)- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Chloro(trichloromethyl)sulfine, Cl3C(Cl)C=SOThe unstable trichlorothioacetyl chloride (2) could be trapped by a Diels-Alder reaction with anthracene to form the adduct 3, which in turn could be oxidized to the corresponding sulfine adduct 4. Finnaly, chloro(trichloromethyl)sulfine (5) was prepared in good yield by vacuum thermolysis (retro Diels-Alder reaction) of 4.
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    Organophosphorverbindungen, 48. 1-Halogen-1H-phosphirene aus Phosphaalkinen und Halogencarbenen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1207-1213 
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    ISSN: 0009-2940
    Keywords: Diazirines ; Phosphaalkynes ; Carbenes ; Phosphirenes ; [2 + 1] Cycloaddition ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organophosphorus Compounds, 48. - 1-Halogen-1H-phosphirenes from Phosphaalkynes and ChlorocarbenesHalogen-substituted carbenes (7a - i), generated by thermolysis of diazirines (11a-i), add onto phosphaalkynes (8a-c) to form the title compounds (10a-1). Initially formed 2H-phosphirenes (9) could not be detected as their subsequent conversion to the 1H-isomers 10 by a 1,3-halogen shift is very fast. Hydrolysis of 10c,e,g-i and k yields vinylphosphonous acids (17a - e). 1-Chloro-1H-phosphirenes are transformed by nucleophilic substitution into fluoro (10a,c,e → 19a-c), bromo (10c,e → 20a,b), and iodo analogs (10c,e → 21a,b) with the help of silver tetrafluoroborate, trimethylsilyl bromide, and trimethylsilyl iodide, respectively. A crystal structure analysis of 10c is reported.
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    Organische Synthesen mit übergangsmetall-Komplexen, 51. 1-Metalla-1,3,5-triene und 1-Metalla-1,3-dien-5-ine von Chrom und Wolfram durch Insertion von Alkinen in M=C- bzw. C=C-Bindungen von 1-Metalla-1,3-dienen bzw. 1-Metalla-1-en-2-inen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1229-1236 
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    ISSN: 0009-2940
    Keywords: Carbene complexes of chromium and tungsten ; 1-Metalla-1,3,5-trienes ; 1-Metalla-1,3-dien-5-ynes ; Insertion of alkynes into M=C and C=C bonds ; [2 + 2] Cycloaddition reactions of carbene complexes and alkynes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organic Syntheses via Transition Metal Complexes, 51. - 1-Metalla-1,3,5-trienes and 1-Metalla-1,3-dien-5-ynes of Chromium and Tungsten by Insertion of Alkynes into M=C and C=C Bonds of 1-Metalla-1,3-dienes and 1-Metalla-1-en-3-ynes, respectively1-Metalla-1,3,5-trienes LnM=C(NEt2)-C(Me)—C(OEt)-CH=CHPh (3,4) and LnM=C(OEt)- CH=C(NEt2) - C(Me)=CHPh [5, LnM=Cr(CO)5 (a), W(CO)5 (b)] are obtained for the first time from the corresponding 1-metalla-1,3-dienes LnM=C(OEt) - CH=CHPh (1a, b) under very mild conditions by the insertion of the electron-rich alkyne Et2N-C ≡ C - Me (2) into the M=C and the C=C bonds, respectively, of 1. The chelate complex (6b) and the cyclobutenyl carbene complex 7b are isolated as minor side products. 1-Metalla-1,3-dien-5-ynes LnM=C(NEt2) - C(Me)=C(OEt) - C ≡ CPh [9, 10, LnM=Cr(CO)5 (a), W(CO)5 (b)] are formed with high regio- and stereoselectivity on insertion of 2 into the M=C bonds of 1-metalla-1-en-3-ynes 8. X-ray data are given for the tungsten complex 3b.
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    Gas-Phase Thermolysis, 14. On the Isomerization of Dimethyl Carbonate and Its Mono-, Di-, and Trithio Analogs (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1265-1270 
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    ISSN: 0009-2940
    Keywords: Gas-phase pyrolysis ; Tandem mass spectrometry ; Carbonates ; Alkyl migration ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Gas-phase pyrolysis of dimethyl carbonate and its mono-, di-, and trithio analogs has been performed in the temperature range from 1253 to 1404 K applying the gas phase Curie-point pyrolysis technique. Real-time analyses have been carried out by means of mass-spectrometric techniques. The possible isomerizations of the ester functions have been studied by collisional activation mass spectrometry in combination with appropriate D, 18O, and 34S labeling. It is demonstrated that methyl group migrations can be induced pyrolytically in cases where oxygen-to-oxygen or oxygen-to-sulfur isomerizations are involved; in contrast, sulfur-to-oxygen as well as sulfur-to-sulfur isomerizations apparently do not take place.
    Additional Material: 7 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240546
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    Masthead (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991) 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240601
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  • 184
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    Chiral Vinyl Anions for “Carbonyl Umpolung”. Highly Stereoselective Addition of a Novel Enantiomerically Pure Vinyllithium Reagent to Aldehydes (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1379-1395 
    Details
    ISSN: 0009-2940
    Keywords: Vinyl anions, chiral ; Umpolung ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The vinyllithium reagent 13 and its enantiomer are generated by a bromine/lithium exchange reaction starting from dibromoalkenes 11 and 12, both available from the corresponding enantiomer of alkyl lactate. When 13 is allowed to react with aldehydes or with acetophenone, a highly stereoselective addition to the Re face of the carbonyl compounds occurs to give predominantly the diastereomers 15. Alkenes 25a,c, accessible by another bromine/lithium exchange reaction of 15a,d and subsequent protonation, can be cleaved by ozonolysis followed by reduction to afford carbinols 27a, b in 〉 98% ee. The sequence corresponds to a stereoselective introduction of a methanol d1 synthon (⊖CH2OH) or, as shown by other examples, of acyl and formyl d1 synthons (⊖CRO and ⊕CHO) into prochiral carbonyl compounds. As a consequence, 13 and its enantiomer may be regarded as highly stereoselective reagents for "carbonyl umpolung". A series of further vinyllithium reagents, 38a-g and 54/55, is treated with benzaldehyde, but none of those displays comparable enantiofacial selectivity. The prerequisites to the highly stereoselective reactions of 13 and its enantiomer are briefly discussed.
    Additional Material: 3 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19911240612
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  • 185
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    Electron Diffraction Study of the Molecular Structure of 1,3-Diphenylpropane-1,2,3-trione (Diphenyl Triketone) (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1411-1414 
    Details
    ISSN: 0009-2940
    Keywords: Propane-1,2,3-trione, 1,3-diphenyl- ; Electron diffraction ; Gas-crystal structure comparison ; Conformation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The molecular structure of 1,3-diphenylpropane-1,2,3-trione (diphenyl triketone) has been determined by gas-phase electron diffraction at 130°C nozzle temperature. It has been found that the phenyl rings are nearly coplanar with the adjacent carbonyl groups, and the two Cph-C(O)-C(O)-C(O) dihedral angles are - 129.5 ± 0.8 and - 107.1 ± 0.8° (0° corresponds to the syn form). Bond distances (rg, Å) and bond angles (deg) with estimated total errors are C—H 1.105 ± 0.006, O = C 1.213 ± 0.003, 〈 Cph-Cph〉 1.404± 0.003, Cph-C(O) 1.478 ± 0.005, C(O)-C(O) 1.558 ± 0.004, Cph-C(O)-C(O) 120.0 ± 0.3, Cph—C(O)=O 120.8 ± 0.4, C(O)-C(O)-C(O) 117.3 ± 0.4, Cph-Cph(CO)-Cph 119.8 ± 0.6. Although there is a general agreement between the gas-phase and crystal molecular structures there are some notable differences. One of the benzene rings is slightly turned about the Cph-C(O) axis in the opposite direction in the gas molecule as compared to the crystal. This causes a marked shortening of the O… H intramolecular contact (to 2.18 Á) between the central oxygen and an ortho-hydrogen.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240615
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  • 186
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    Ring Fragmentation of Benzotriazol-1-yl Carbanions (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1431-1434 
    Details
    ISSN: 0009-2940
    Keywords: Proton transfer ; Fragmentation of rings ; Aryllithium ; Carbanions ; Imines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title carbanions 1 are shown to lose nitrogen to afford ortho-carbiminophenyl anions 4 which can be protonated by inter- or intramolecular proton transfer or react inter- or intramolecularly with other types of electrophilic center.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19911240618
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    Die Bildungsenthalpie des Allyl- und Methallyl-Radikals (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1453-1460 
    Details
    ISSN: 0009-2940
    Keywords: Shock tube technique ; Oxygen scavanger ; Heat of formation ; Allyl resonance energy ; Radical disproportionation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Heat of Formation of the Allyl and Methallyl RadicalThe decomposition of 1,5-hexadiene (1), 2-methyl-1,5-hexadiene (7), and 2,5-dimethyl-1,5-hexadiene (5) into allyl- (2) and methallyl radicals (6) was studied by means of the shoke tube technique with and without oxygen as scavanger. From these data and from the temperature dependence of the equilibria 1 ⇌ 2 and 5 ⇌ 6, measured between 600 and 800°C, the heat of formation of the allyl (2) and methallyl radical (6) as well as the activation parameters for the recombination and disproportionation of these radicals have been deduced.
    Additional Material: 4 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240621
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  • 188
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    Rotationsbarrieren Vinyl-substituierter Olefine (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1461-1470 
    Details
    ISSN: 0009-2940
    Keywords: Allyl stabilisation energy ; Calculations, force field ; Rotational barrier, intrinsic ; Gas-phase kinetics ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Rotational Barriers of Vinyl-Substituted OlefinesFor the vinyl-substituted olefines 1 - 14 activation parameters for the geometrical isomerisation have been determined in the gas-phase. By comparison of these barriers with the corresponding ones of the isolated double bonds, each corrected by the contribution of the steric energy to the ground and transition state, a value of 13.5 ± 1.1 kcal mol-1 for the allyl stabilisation energy (ASE), defined as replacement of alkyl by vinyl, has been derived.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240622
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    Neue planare π-Systeme, II1) Zur Darstellung und Struktur von Tetrakis(phenylethinyl)ethen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1471-1475 
    Details
    ISSN: 0009-2940
    Keywords: Polyacetylenes ; Cross conjugation ; Alkenes, tetraethynyl ; π-Systems, planar ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New Planar π-Systems, II1). - On the Preparation and Structure of Tetrakis(phenylethynyl)etheneThe preparation of tetrakis(phenylethynyl)ethene (1 b) has been repeated. Among various routes to this highly unsaturated cross-conjugated π-system, the dimerization of bromide 2 via the carbene 3 is the most simple one. Full spectroscopic data for 1 b are reported for the first time, as is its X-ray structural analysis at - 95°C.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240623
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    Kurzmitteilung/Short Communication Generation and Trapping of Dichlorothioketene (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1485-1487 
    Details
    ISSN: 0009-2940
    Keywords: Thioketenes ; Flash-vacuum pyrolysis ; Diels-Alder reaction ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Flash-vacuum pyrolysis of 2,4-bis(dichloromethylene)-1,3-dithietane (1) at 820°C furnishes dichlorothioketene (2a) which may be trapped with cyclopentadiene (3) in a [4+2] cycloaddition. The constitution 4a of the product is confirmed by an X-ray structural analysis of the related cycloadduct 4b.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240626
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    Bis[2,3-naphthalindiolato(2-)](pyrrolidiniomethyl)silicat-Acetonitril-Solvat: Synthese sowie Kristall- und Molekülstruktur eines zwitterionischen λ5-SpirosilicatsHerrn Professor Ernst Mutschler zum 60. Geburtstag gewidmet. (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1491-1496 
    Details
    ISSN: 0009-2940
    Keywords: Spirosilicates, zwitterionic ; Bond cleavage, Si - C ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bis[2,3-naphthalenediolato(2 - )](pyrrolidiniomethyl)silicate Acetonitrile Solvate: Synthesis and Crystal and Molecular Structure of a Zwitterionic λ5-SpirosilicateThe zwitterionic spirocyclic bis[2,3-naphthalenediolato[2-)](pyrrolidiniomethyl)silicate (3) was synthesized and the crystal and molecular structure of its acetonitrile solvate 3 · CH3CN investigated. 3 was prepared by reaction of trimethoxy(pyrrolidinomethyl)silane (8) or dimethoxy(methyl)(pyrrolidinomethyl)silane (8) or dimethoxy(methyl)(pyrrolidinomethyl)silane (9) with 2,3-dihydroxynaphthalene in acetonitrile. Reaction 9 → 3 involves a remarkable Si - C cleavage with formation of CH4. The pentacoordinate silicon atom of 3 · CH3CN is surrounded by 4 oxygen atoms and 1 carbon atom, the latter being in an equatorial position. The coordination polyhedron can be described as a distorted trigonal bipyramid (the structure is displaced by 20.5% from the trigonal bipyramid towards the square pyramid). The crystal lattice of 3·CH3CN contains centrosymmetric dimers of 3, built up by intermolecular N - H … O hydrogen bonds.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240702
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    Chemie des Dicyans: Reaktionen von Diiminosuccinonitril (DISN) mit Sulfenylchloriden und Chlortrimethylsilan sowie Cyclisierung zu Trifluormethyl-substituierten 2H-Imidazolen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1517-1520 
    Details
    ISSN: 0009-2940
    Keywords: Diiminosuccinonitrile ; 2H-Imidazoles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemistry of Cyanogen: Reactions of Diiminosuccinonitrile (DISN) with Sulfenyl Chlorides, Chlorotrimethylsilane and Ring Closure to Trifluoromethyl-Substituted 2H-Imidazoles4,5-Dicyano-2-hydroxy-2-(trifluoromethyl)-2H-imidazole (1) is easily prepared by treating DISN with trifluoroacetic anhydride. In the presence of 4-(dimethylamino)pyridine, however, the O-acylated derivative 2 is formed in excellent yield, while the reaction of 1 with chlorotrimethylsilane affords the O-silylated product 6. A bi-1,2,5-thiadiazole of the formula S2(CN)4Cl2 (5) is the final reaction product, when DISN is treated with sulfur dichloride in the presence of “naked” chloride ions. On the other hand the non-heterocyclic N-sulfenyl derivative 4 has readily been obtained, when DISN is treated with F3CSCl instead. Finally a procedure is described to convert DISN into the corresponding N-silylated diimine 3.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240706
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    Complexes with sterically demanding ligands, XVI. An unexpected coupling of trimethylsilyl-substituted cyclopentadienide anion by ferric chloride (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1575-1577 
    Details
    ISSN: 0009-2940
    Keywords: Oxidative coupling of cyclopentadienide anion ; Dihydrofulvalene, molecular structure ; Migration of trimethylsilyl group ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of 1,2,4-tris(trimethylsilyl)cyclopentadienyllithium with ferric chloride in THF at -95°C leads to the formation of a thermally sensitive iron(III) complex which decomposes to the new dihydrofulvalene derivative 3,7-dihydro-1,3,3,5,7,7-hexakis(trimethylsilyl)fulvalene (1).
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240716
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    An easy access to (S)- and (R)-hydroxycyclohexenone (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1677-1678 
    Details
    ISSN: 0009-2940
    Keywords: Cyclopentadienes, chiral ; Quinone adducts ; Diels-Alder reactions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Diels-Alder adduct obtained by addition of quinone to the chiral cyclopentadiene 2 undergoes regioselective and stereoselective reduction after hydrogenation. The 4-hydroxy ketone 3 thus formed yields the title compound 1 in a thermal retro Diels-Alder process.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240732
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    Kurzmitteilung/Short Communication Darstellung und Eigenschaften von und Reaktionen mit metallhaltigen Heterocyclen, LXXV Synthese eines Diphosphamolybdacyclopentens durch Alkin-Insertion in die P - P-Bindung eines Diphosphamolybdacyclopropans (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1715-1716 
    Details
    ISSN: 0009-2940
    Keywords: P - P bond ; Alkyne insertion ; Diphosphamolybdacyclopentene ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Metal-Containing Heterocycles: Preparation, Properties, Reactions, LXXV1).  -  Synthesis of a Diphosphamolybdacyclopentene by Alkyne Insertion into the P - P Bond of a DiphosphamolybdacyclopropaneInsertion of the alkyne RC≡CR (R = CO2Me) into the P - P bond of the diphosphamolybdacyclopropane (5-C5H5)-(OC)2Mo-PPh2-PAr (2) [Ar = 2,4,6-(tBu)3C6H2] results in the formation of the thermally and kinetically stable diphosphamolybdacyclopentene (η5-C5H5)(OC)2Mo-PPh2-RC = CR-PAr (3), which is characterized on the basis of mass, IR, 31P{1H}-, 1H-, and 13C{1H}-NMR spectra.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240808
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    Lösliche bisaxial substituierte (Phthalocyaninato)ruthenium-Komplexe (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1733-1738 
    Details
    ISSN: 0009-2940
    Keywords: Phthalocyanine ; Ruthenium complexes ; Pyridines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Soluble Bisaxially Substituted (Phthalocyaninato)ruthenium ComplexesSeveral attempts to prepare (tBu4Pc)Ru only led to an impure product (tBu4Pc)RuLx. This reacts quantitatively with pyridine to form (tBu4Pc)Ru(py)2, easily purified by chromatography. In addition the preparation of (tBu4Pc)RuL2 with L = pyridine, 2-picoline (2-pic), 3-picoline (3-pic), 4-picoline (4-pic), 2,5-lutidine (2,5-lut), and 2,6-lutidine (2,6-lut), respectively, is described. All complexes are characterized by spectroscopic methods including 1H-NMR spectroscopy. Not even in the cases of (tBu4Pc)RuL2 with L = 2-pic and 2,5-lut, a careful removal of the ligands L by thermogravimetric methods (TG/DTA) leads to pure (tBu4Pc)Ru. For comparison, the bisadducts PcRuL2 with L = pyridine, picolines (2-pic, 3-pic, 4-pic), lutidines (2,3-lut, 2,5-lut, 2,6-lut), and chloropyridines (2-Clpy and 3-Clpy), respectively, are prepared by treatment of PcRu with an excess of the ligand. For the first time (phthalocyaninato)iron complexes PcFeL2 with sterically hindered axial ligands, e.g. PcFe(2-pic)2, are prepared and characterized by 57Fe Mößbauer spectroscopy.
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    URL: http://dx.doi.org/10.1002/cber.19911240811
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    o-(α-Benzotriazolylalkyl)phenols: Versatile Intermediates for the Synthesis of Substituted Phenols (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1809-1817 
    Details
    ISSN: 0009-2940
    Keywords: Lithiation ; Mannich reaction ; Alkylation ; Grignard reaction ; Condensation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Phenols and naphthols are benzotriazolylmethylated by 1-(hydroxymethyl)-1H-benzotriazole (13) (a formaldehyde derivative) in the o- or (if both o-positions are occupied) in the p-position. The reaction can be extended to other aldehydes in the case of the naphthols. The methylene group in the o-(benzotriazolylmethyl)phenols can be lithiated (but only after trimethylsilyl protection of the hydroxy group) and then substituted by various electrophiles. The benzotriazole residues in both the primary products and in their substituted derivatives can be displaced by the alkyl anions of Grignard reagents or by hydride ions allowing the elaboration of many new types of substituted phenols.
    Additional Material: 5 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19911240818
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    Cyclopropannelation of the Bicyclo[3.3.0]octane Framework. On the Chemical Significance of exo-Positioned Substituents (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1827-1830 
    Details
    ISSN: 0009-2940
    Keywords: Cyclopropannelation ; Bicyclo[3.3.0]octane derivatives ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: To facilitate the synthesis of tetracycles containing the framework 2, the reaction of the tetrabromide 8 with cyanide and bis(phenylsulfonyl)methane under various conditions was investigated. Instead of the expected twofold bridging, novel cyclopropa derivatives were obtained. Product formation is a consequence of the stereochemistry of the starting material 8, with the exo configuration of the bromomethyl substituents being the crucial factor.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240820
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    Alkylations of (R,R)-2-t-Butyl-6-methyl-1,3-dioxan-4-ones which are not Possible with Lithium Amides may be Achieved with a Schwesinger P4 Base (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1837-1843 
    Details
    ISSN: 0009-2940
    Keywords: β-Hydroxycarboxylic acids, α-alkylation of ; EPC synthesis ; 1,3-Dioxan-4-ones, enolates of ; Enolates, naked ; Schwesinger's base ; Phosphazene P4 base ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enolates A of the dioxanones specified in the title, when generated with lithium amide bases, can only be alkylated with highly reactive electrophiles, and only once. With Schwesinger's t-Bu-P 4 base (a very strong, so-called neutral base, containing 4P and 13N atoms capable of bearing a positive charge in the conjugate P4H+ cation) the dioxanone 1 can be doubly alkylated even with iodobutane (products 16, 17). The 5,6-dimethyl- and 5-benzyl-6-methyldioxanone 2 and 3 can be alkylated diastereoselectively with the formation of quaternary centers at C(5) (products 4, 8 - 14). In one case, the configuration of the product 4 obtained was determined by conversion to a β-lactone 6 and an olefin 7 (a previous assignment had to be revised). Even the 2,5,6,6-tetraalkyl-substituted dioxanone 19 could be further alkylated (→ 20 + 21). Five of the new alkylation products were hydrolyzed to the parent 3-hydroxy-carboxylic acids 5, 22  -  25. The enormous reactivities achieved with the inherently labile enolates and the P411+ counterions are discussed.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19911240822
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    Reaktionen von Dienolaten des (R)-2-tert-Butyl-6-methyl-4H-1,3-dioxin-4-ons mid Aldehyden und Ketonen  -  ein chirales Acetessigester-d4-Reagens (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1845-1852 
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    ISSN: 0009-2940
    Keywords: (R)-3-Hydroxybutyric acid ; Aldol addition, regioselective, steric course of ; 1,3-Dioxin-4-ones, lithium dienolates of ; EPC synthesis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Dienolates from (R)-2-tert-Butyl-6-methyl-4H-1,3-dioxin-4-one with Aldehydes and Ketones  -  a Chiral Acetoacetic Ester d4-Reagent
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    URL: http://dx.doi.org/10.1002/cber.19911240823
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