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  • 1
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m. n]Phanen, 27. Modelle für Excimere und Exciplexe: [2.2]Phane des Fluorens, 9-Fluorenons und 9-Fluorenyl-Anions (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 144-162 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m. n]Phanes, 27. Models for Excimers and Exciplexes: [2.2]Phanes of Fluorene, 9-Fluorenone, and 9-Fluorenyl Anionanti- and syn-[2.2](2,7)-fluorenophane (1, 2) as well as their 5,16-dioxo and 5-oxo derivatives 3, 5, and 6 containing two or one 9-fluorenone units were synthesized: Cyclisation of the bis(bromomethyl) compounds 7 and 10 with the bis(mercaptomethyl) compounds 9 and 12 gave the dithia[3.3]phanes 14, 16, and 18 containing fluorene and 9-fluorenone units bridged at the 2,7-positions. Oxidation to the disulfones 15, 17, and 18 and vapour phase pyrolysis (500°C, 0.1 Torr) led to 1/2, 3, and 5/6, respectively. The molecular geometry of 1 was determined by X-ray structure analysis. On treatment of suspensions of 1 and 2 in hexamethylphosphoric triamide with n-butyllithium in n-hexane red solutions of the dianions 21 and 22 were generated, which were characterized by 1H NMR spectroscopy. With deuterium oxide the dianion 22 yielded [exo-5, exo-16-D2]-anti-[2.2](2,7)fluorenophane (24), with methyl iodide exo-5, exo-16-dimethyl-anti-[2.2](2,7)fluorenophane (26). Multiple metalation with n-butyllithium and reaction with methyl iodide led to 5,5,16,16-tetramethyl-anti-[2.2](2,7)fluorenophane (27).
    Notes: anti- und syn-[2,2](2,7)Fluorenophan (1, 2) sowie ihre 5,16-Dioxo- und 5-Oxoverbindungen 3, 5 und 6 mit zwei bzw. einer 9-Fluorenon-Einheit wurden synthetisiert: Cyclisierung der Bis(brommethyl)-Verbindungen 7 und 10 mit den Bis(mercaptomethyl)-Verbindungen 9 und 12 ergab die Dithia[3.3]phane 14, 16 und 18 mit in 2,7-Position verbrückten Fluoren- und 9-Fluorenon-Einheiten. Oxidation zu den Disulfonen 15, 17 und 18 und Gasphasen-Pyrolyse (500°C, 0.1 Torr) führte zu 1/2, 3 bzw. 5/6. Die Molekülgeometrie von 1 wurde durch Röntgenstrukturanalyse bestimmt. Suspensonen von 1 und 2 in Hexamethylphosphorsäuretriamid ergaben mit n-Butyllithium in n-Hexan rote Lösungen der Dianionen 21 und 22, die durch 1H-NMR-Spektroskopie charakterisiert wurden. Aus dem Dianion 22 erhielt man mit Deuteriumoxid [exo-5, exo-16-D2]-anti-[2.2](2,7)Fluorenophan (24), mit Methyliodid exo-5, exo-16-Dimethyl-anti-[2.2](2,7)fluorenophan (26). Mehrfache Metallierung mit n-Butyllithium und Reaktion mit Methyliodid führte zu 5,5,16,16-Tetramethyl-anti-[2.2](2,7)fluorenophan (27).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180115
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  • 2
    Electronic Resource
    Electronic Resource
    Kleine Ringe, 50. Ungewöhnliche Dimerisierung von Tri-tert-bytylcyclobutadien (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 409-412 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Small Rings, 50. Unusual Dimerization of Tri-tert-butylcyclobutadieneThe dimerization of tri-tert-butylcyclobutadiene (2) does not lead to syn-dimer 4 but  -  as shown by a X-ray structure determination  -  via a two-step process to the unexpected anti-configurated dimer 5.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180141
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  • 3
    Electronic Resource
    Electronic Resource
    Deformation Density of a cis,cis-Trialkyltriaziridine (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 175-178 
    Details
    ISSN: 0009-2940
    Keywords: cis,cis-Trialkyltriaziridine ; Deformation density of cis,cis-Trialkyltriaziridine ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Deformationsdichte eines cis,cis-TrialkyltriaziridinsAuf der Basis von Tieftemperatur-Röntgebeugungsdaten (105 K) haben wir die Deformationsdichte von 6,8,9-Triacetoxy-2,3,4-triazatetracyclo[3.3.1.02,4.03,7] nonan (1) bestimmt. Mit der X-X-Methode konnten keine signifikanten Elektronendichtemaxima auf den stark gebogenen N—N-Bindungen gefunden werden. Die Dichtemaxima an den einsamen Elektronenpaaren der Stickstoffatome und in den C—C-, C—N- und C—O-Bindungen traten klar hervor.
    Notes: We determined the deformation densities of 6,8,9-triacetoxy-2,3,4-triazatetracyclo[3.3.1.02,4.03,7] nonane (1), a triaziridine derivative, from low temperature X-ray data (105 K). Significant electron density peaks of the strongly bent N—N bonds of the triaziridine ring could not be found by the X-X method. The density maxima of the lone pairs of the nitrogen atoms and of the C—C, C—N and C—O bonds appear clearly.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220127
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  • 4
    Electronic Resource
    Electronic Resource
    mini-chiuz (1985)
    Weinheim : Wiley-Blackwell
    Chemie in unserer Zeit 19 (1985), S. A74 
    Details
    ISSN: 0009-2851
    Keywords: Chemistry ; Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ciuz.19850190607
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  • 5
    Electronic Resource
    Electronic Resource
    Transanulare Wechselwirkung bei [m.n]Phanen, 29. Modelle für Amin-Aromaten-Exciplexe: π-π- versus n-π-Wechselwirkung bei isomeren [2]Naphthalino[2](2,6)pyridinophanen und [2]Naphthalino[2](2,6)pyridinophan-1,11-dienen (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 4884-4906 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Transanular Interaction in [m.n]Phanes, 29. Models for Amine-Arene-Exciplexes: π-π versus n-π Interaction in Isomeric [2]Naphthalino[2](2,6)pyridinophanes and [2]Naphthalino[2](2,6)pyridinophane-1,11-dienesThe [2.2]naphthalinopyridinophanes 5, 6 and the corresponding dienes 3, 4 were synthesized as models for exciplexes. From the dithia[3.3]phanes 10 and 12, prepared by cyclisation of 7 with 9 and 8 with 9, the [2.2]phanes 5 and 6 were obtained by oxidation to the disulfones 11, 13 followed by vapour phase pyrolysis. Ring contraction of 10, 12 by S-analogous Wittig ether rearrangement led to 14/15 and 17/18, respectively. 14 and 17 were converted into the dienes 3 and 4 via oxidation to the sulfoxides 16, 19 and pyrolytic elimination of methanesulfenic acid. The 1H NMR data correspond to the perpendicular orientation of pyridine and naphthalene in 3, 4 and to more parallel arrangements of the aromatic units in 5, 6. For the conformational flipping of the pyridine ring in 5 an energy barrier of ΔH± = 11.84 ± 0.15 kcal/mol and ΔS± = -1.70 ± 0.58 cal K-1 mol-1 was obtained by temperature dependent 1H NMR and line shape analysis. The molecular structures of 3, 5, and 6 were determined by X-ray analysis. Absorption spectra and especially the red-shifted structureless fluorescence emissions typical for exciplexes show orientational dependencies and are discussed in terms of n-π interaction between pyridine nitrogen and naphthalene in 3, 4 and π-π interaction between the aromatic units in 5, 6.
    Notes: Als Exciplex-Modelle wurden die [2.2]Naphthalinopyridinophane 5, 6 und die entsprechenden Diene 3, 4 synthetisiert: Aus den Dithia[3.3]phanen 10 und 12, dargestellt durch Cyclisierung von 7 mit 9 und 8 mit 9, wurden die [2.2]Phane 5 und 6 durch Oxidation zu den Disulfonen 11, 13 und deren Pyrolyse in der Gasphase erhalten. Ringverengung von 10, 12 durch S-analoge Wittig-Etherumlagerung ergab 14/15 bzw. 17/18. 14 und 17 wurden durch Oxidation zu den Sulfoxiden 16, 19 und pyrolytische Eliminierung von Methansulfensäure in die Diene 3 und 4 übergeführt. Die 1H-NMR-Daten entsprechen der senkrechten Anordnung von Pyridin und Naphthalin in 3, 4 und mehr parallelen Orientierungen der Aromaten-Einheiten in 5, 6. Temperaturabhängige 1H-NMR und Linienformanalyse ergaben für das Umklappen des Pyridin-Ringes in 5 eine Energiebarriere von ΔH± = 11.84 ± 0.15 kcal/mol und ΔS± = -1.70 ± 0.58 cal K-1 mol-1. Die Molekülstrukturen von 3, 5 und 6 wurden durch Röntgenstrukturanalyse bestimmt. Absorptionsspektren und vor allem die für Exciplexe typisch rotverschobenen und strukturlosen Fluoreszenz-Emissionen von 3-6 zeigen Orientierungsabhängigkeiten und werden mit n-π-Wechselwirkung zwischen dem Pyridin-Stickstoff und Naphthalin in 3, 4 und π-π-Wechselwirkung zwischen den Aromaten-Einheiten in 5, 6 interpretiert.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181223
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  • 6
    Electronic Resource
    Electronic Resource
    Kondensierte Ringsysteme, XVIII Zur Synthese von Cyclobuten-Derivaten aus den entsprechenden Thiolanen - Kristall- und Molekülstruktur von 2,5-o-Benzeno-3,4-benzo[4.2.2]propella-3,7,9-trien (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 5-9 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cyclobutene derivatives are prepared from the corresponding thiolanes in better yields by using the chloro sulfoxides than the chloro sulfones, which are intermediates in the Ramberg-Bäcklund reaction. This is established by the synthesis of 2,5-o-benzeno-3,4-benzobicyclo[4.2.0]octa-3,7-diene (6) from 2,5-o-benzeno-3,4-benzo-8-thiabicyclo[4.3.0]non-3-ene (1). On the same way 2,5-o-benzeno-3,4-benzo[4.2.2]propella-3,7,9-triene (8) can now be prepared in better yields and its X-ray structure analysis is described.
    Notes: Cyclobuten-Derivate lassen sich aus den entsprechenden Thiolanen über die Chlorsulfoxide in besseren Ausbeuten herstellen als über Chlorsulfone, die bei der Ramberg-Bäcklund-Reaktion als Zwischenprodukte auftreten. Dieses wird durch die Synthese von 2,5-o-Benzeno-3,4-benzobicyclo[4.2.0]octa-3,7-dien (6) aus 2,5-o-Benzeno-3,4-benzo-8-thiabicyclo[4.3.0]non-3-en (1) bewiesen. Auf dem gleichen Syntheseweg konnte jetzt auch das 2,5-o-Benzeno-3,4-benzo[4.2.2]propella-3,7,9-trien (8) in besserer Ausbeute erhalten werden, dessen Röntgenstrukturanalyse beschrieben wird.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200103
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  • 7
    Electronic Resource
    Electronic Resource
    Darstellung, Struktur und Eigenschaften von 1,6-Cyclodecadiin. Vergleich mit 1,5-Cyclooctadiin und 1,7-Cyclododecadiin (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 735-740 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation, Structure, and Properties of 1,6-Cyclodecadiyne.  -  Comparison with 1,5-Cyclooctadiyne and 1,7-Cyclododecadiyne1,6-Cyclodecadiyne (3) is synthesized starting from naphthalene or decaline, respectively. X-ray investigations reveal a chair conformation for 3 in the crystal. The transannular contacts (2.991 Å) between the parallel arranged acetylene units cause a cisoid bending (bond angle 171.7°). The homologous 1,7-cyclododecadiyne (4) shows a twisted chair-chair like conformation in which both acetylene moieties cross each other by an angle of 24°. The cisoid deformation of the acetylene moieties (173.8°) is due to the unfavourable conformation of 4. The photoelectron (PE) spectrum of 4 only two strongly overlapping bands are found in the low energy region. The difference in the PE spectra between 3, 4 and 1,5-cyclooctadiyne (2) is rationalized as due to conformational effects (3-4) and π/σ interactions (2-3), respectively.
    Notes: Ausgehend von Naphthalin bzw. Decalin werden zwei Wege zur Synthese von 1,6-Cyclodecadiin (3) beschrieben. Röntgenstrukturuntersuchungen zeigen, daß 3 in einer Sesselkonformation im Kristall vorliegt. Die parallel angeordneten Acetylengruppen sind aufgrund transannularer Kontakte von 2.991 Å aus der linearen Anordnung cisoid deformiert (Bindungswinkel 171.7°). Das homologe 1,7-Cyclododecadiin (4) zeigt eine verdrillte Sessel-Sessel-Konformation, in der die beiden Acetylengruppen unter einem Winkel von 24° gekreuzt zueinander angeordnet sind. Die cisoide Deformation der Acetylengruppen (173.8°) ist durch die ungünstige Konformation bedingt. Das Photoelektronen-(PE)-Spektrum von 3 zeigt vier deutlich aufgespaltene π-Banden, während im PE-Spektrum von 4 nur zwei stark überlappende Banden im Bereich niederer Energie gefunden werden. Der Unterschied der PE-Spektren zwischen 3, 4 und 1,5-Cyclooctadiin (2) wird auf konformative Effekte (3-4) bzw. π/σ-Wechselwirkungseffekte (2-3) zurückgeführt.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881210421
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  • 8
    Electronic Resource
    Electronic Resource
    Nichtbindende Wechselwirkungen in zwei 7-Spirotetracyclo[4.1.0.02,4.03,5]heptanen (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 695-701 
    Details
    ISSN: 0009-2940
    Keywords: Nonbonded interactions ; Spirotetracyclo[4.1.0.02,4.03,5]heptanes ; Long-range coupling constants ; 5H-Dibenzo[a,d]cycloheptene, 10,11-dihydro- ; 1-Pyrazolines, nitrogen extrusion ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Nonbonded Interactions in Two 7-Spirotetracyclo[4.1.0.02,4.03,5]-heptanesThe reaction of tetrachlorodiazocyclopentadiene with benzvalene (2) gave the fulvene derivative 3. In contrast, treatment of diazofluorene and 5-diazo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene with 2 afforded the expected spiro-1-pyrazolines 4 and 5, respectively. Photolytic extrusion of nitrogen from 4 and 5 led to the corresponding spirotetracycloheptanes 6 and 7. The X-ray structure analysis of 6 revealed a close contact between one hydrogen atom each of the tetracycloheptane and the fluorene subunits. This short distance (2.15 Å) causes an increase in bond angles and is believed to produce strong deshielding of the respective protons and a 0.6-Hz coupling between them, which is formally a long-range coupling across seven bonds. Compound 7 is the first chiral tetracycloheptane. This is due to a nonplanar conformation of the seven-membered ring, which does not invert at room temperature. On the basis of NOE measurements the 1H-NMR signals of 6 and 7 are assigned.
    Notes: Die Reaktion von Tetrachlordiazocyclopentadien mit Benzvalen (2) ergab das Fulven-Derivat 3. Dagegen führten die Umsetzungen von Diazofluoren und 5-Diazo-10,11-dihydro-5H-dibenzo-[a,d]cyclohepten mit 2 zu den erwarteten Spiro-1-pyrazolinen 4 bzw. 5. Die photolytische Abspaltung von Stickstoff aus 4 und 5 lieferte die Spirotetracycloheptane 6 bzw. 7. Die Röntgenstrukturanalyse von 6 beweist einen engen Kontakt zwischen je einem Wasserstoffatom der Tetracycloheptan- und der Fluoren-Einheit. Dieser kurze Abstand (2.15 Å) ruft Winkelaufweitungen hervor und wird auch als Grund für starke Entschirmungen der betreffenden Protonen und eine formal über sieben Bindungen reichende 0.6-Hz-Kopplung zwischen ihnen angesehene. 7 ist das erste chirale Tetracycloheptan. Ursache dafür ist eine nichtebene Konformation des Siebenrings, der bei Raumtemperatur nicht invertiert. Auf der Basis von NOE-Messungen gelang die Zuordnung der 1H-NMR-Signale von 6 und 7.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220416
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  • 9
    Electronic Resource
    Electronic Resource
    On the Purported Structure of Cyclodeca[1,2,3-de: 6,7,8-d′e′]dinaphthalene (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 480-487 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of the bis(sulfonium salt)7 in a solution of Na2CO3 in H2O/EtOH yielded three main products 8-10. The spectroscopic data of 8 were identical to those which led Mithcell and Sondheimer to assign them to cyclodeca[1,2,3-de: 6,7,8-d′e′]dinaphthalene (3). Our investigations show, however, that the correct structural assignment leads to the structure of 7,7a-dihydrodibenzo[de,mn]naphthacene (8).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700228
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis and Properties of 1,5-Dimethyltricyclo[3.3.0.02,8]octane- and 1,5-Dimethyltetracyclo[3.3.0.02,804,6]octane Derivatives (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 71-84 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of 1,5-dimethyltricyclo[3.3.0.02,8]octane-3,7-dione (2), 1,5-dimethyltetracyclo[3.3.0.02,804,6]-octane-3,7-dione (3), the corresponding dienes 5 and 6 as well as the mixed enones 13-15 is reported. Using He(I) photoelectron spectroscopy (PE) as a tool, a considerable interaction between the n orbitals on the O-atoms and the σ frame in 2 and 3 as well as of the double bonds in 5 and 6 and the σ frame is found. These interactions are also traced back by the electronic absorption spectra of these compounds. The molecular structures of 2 and 3 have been investigated by X-ray analysis.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690111
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