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  • 1
    Electronic Resource
    Electronic Resource
    Regioselektive Funktionalisierung nicht aktivierter CH-Bindungen, 4. Photoreaktionen amphiphiler Benzophenon- und Myristinsäurederivate in Micellen und Doppelschichtmembranen (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 597-606 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Regioselective Functionalization of Nonactivated CH-Bonds, 4. - Photoreactions of Amphiphilic Derivatives of Benzophenonecarboxylic Acid and Myristic Acid Derivatives in Micelles and BilayersAmphiphilic derivatives of benzophenonecarboxylic acid and myristic acid in micelles, vesicles, and multilamellar aggregates were photochemically converted into tertiary alcohols, the workup of which yielded mixtures of the isomeric ketomyristic acid methyl esters 5. A slightly increased but none the less low selectivity was found in bilayers in comparison with micelles. Various amphiphilic head groups shifted the center of attack. Low total yields, especially in bilayers, can be attributed to a predominant reaction between the benzophenone substituents. By preparation of the corresponding reference compounds it could be demonstrated that benzhydrols (8a-d) or benzpinacols (9a-c) are not formed in this unexpected reaction.
    Notes: Amphiphile Benzophenon- und Myristinsäurederivate wurden in Micellen, Vesikeln und multilamellaren Aggregaten photochemisch zu tertiären Alkoholen umgesetzt, deren Aufarbeitung zu Gemischen isomerer Ketomyristinsäure-methylester 5 führte. In Doppelschichtmembranen wurde eine gegenüber Micellen geringfügig erhöhte, insgesamt aber niedrige Selektivität erhalten. Die Verwendung unterschiedlicher Amphiphil-Kopfgruppen führte zur Verschiebung des Angriffsschwerpunktes. Die besonders in Doppelschichtmembranen geringen Gesamtausbeuten lassen sich auf eine bevorzugte Reaktion der Benzophenonreste untereinander zurückführen. Durch Darstellung entsprechender Referenzverbindungen konnte gezeigt werden, daß die Bildung von Benzhydrolen (8a-d) oder Benzpinakolen (9a-c) bei dieser unerwarteten Reaktion keine Rolle spielt.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870706
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  • 2
    Electronic Resource
    Electronic Resource
    Conversion of oleic acid to 17- and 18-substituted stearic acid derivatives by way of the „acetylene zipper“ (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 1037-1040 
    Details
    ISSN: 0170-2041
    Keywords: Fatty acid ; Oleic acid ; Stearic acid, 17- and 18-substituted ; Acetylene zipper ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stearolic acid (2) was prepared from oleic acid (1) and converted to 4, 5, and 7 by way of the „acetylene zipper“ reaction. Compounds 5 and 7 were transformed to the (ω - 1) ketones 8 and 9 and dimerized by way of the Glaser coupling reaction to 11 and 12. At daylight, 12 polymerizes to a blue polymer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101178
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  • 3
    Electronic Resource
    Electronic Resource
    Anodische Oxidation organischer Verbindungen, 23 Anodische Addition von Harnstoffen und Ethylenglykol an konjugierte Diene (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 318-327 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Anodic Oxidation of Organic Compounds, 23.  -  Anodic Addition of Ureas and Ethylene Glycol to Conjugated DienesThe anodic addition of 1,3-dimethylurea (4b) to 2,4-hexadiene (9), 2-methyl-2,4-hexadiene (10), 2,5-dimethyl-2,4-hexadiene (11), 1,3-cyclohexadiene (12), 1,4-diphenylbutadiene (13) and trans-stilbene (14) yields 4,5-disubstituted 1,3-dimethylimidazolidin-2-ones 16-23. Analogously 1,3-diphenylbutadiene (4c) adds to 9 to form 5-methyl-1,3-diphenyl-4-(1-propenyl)imidazolidin-2-one (24). Urea (4a) and 1,3-diacetylurea (4d) fail to react as a consequence of their insufficient nucleophilicity, N,N'-diacetylethylenediamine (4h) and 1,2-diacetylhydrazine (4g) do not undergo addition owing to their very low solubility in acetonitrile. In an electrolyte consisting of ethylene glycol/acetonitrile, 2,4-hexadiene (9) and 1,3-butadiene (8) afford the glycol ethers 25-28. The formation of all products can be explained in terms of a radical cation 29 as first intermediate.
    Notes: Die anodische Addition von 1,3-Dimethylharnstoff (4b) an 2,4-Hexadien (9), 2-Methyl-2,4-hexadien (10), 2,5-Dimethyl-2,4-hexadien (11), 1,3-Cyclohexadien (12), 1,4-Diphenylbutadien (13) und trans-Stilben (14) führt zu den 4,5-disubstituierten 1,3-Dimethylimidazolidin-2-onen 16-23. 1,3-Diphenylharnstoff (4c) addiert sich analog an 9 zu 5-Methyl-1,3-diphenyl-4-(1-propenyl)imidazolidin-2-on (24). Harnstoff (4a) und 1,3-Diacetylharnstoff (4d) lassen sich infolge zu geringer Nucleophilie, N,N'-Diacetylethylendiamin (4h) und 1,2-Diacetylhydrazin (4g) infolge zu geringer Löslichkeit in Acetoniril nicht anodisch mit 2,4-Hexadien (9) umsetzen. In einem Elektrolyten aus Ethylenglykol/Acetonitril entstehen aus 2,4-Hexadien (9) und 1,3-Butadien (8) die Glykolether 25-28. Alle Produkte lassen sich über ein primäres Radikalkation 29 erklären.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790304
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  • 4
    Electronic Resource
    Electronic Resource
    Pheromone, 7. Kolbe-Synthese von 29-tert-Butyldimethylsilyloxy-3,11-dimethyl-1-nonacosen, einer Schlüsselverbindung zur Darstellung eines optisch aktiven Sexuallockstoffes der Deutschen Hausschabe (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1532-1542 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Pheromones, 7.  -  Kolbe Synthesis of 29-tert-Butyldimethylsilyloxy-3,11-dimethyl-1-nonacosene, a Key Intermediate for the Preparation of an Optically Active Pheromone of the German Cockroach29-tert-butyldimethylsilyloxy-3,11-dimethyl-1-nonacosene (17) is synthesized by Grignard coupling of p-tolyl (S)-24-tert-butyldimethylsilyloxy-6-methyl-1-tetracosanesulfonate (15) with 5-bromo-3-methyl-1-pentene (16). The tosylate is prepared from methyl (S)-24-hydroxy-6-methyltetracosanate (11) by protection of the free hydroxyl group and reduction of the ester function. The ester 11 is obtained by twofold Kolbe electrolysis of 18-hydroxyoctadecanoic acid (5) with methyl (S)-3-methylglutarate (6) and with methyl glutarate (9). The bromide 16 is also sythesized from the half-ester 6 by reduction of the ester function and elimination of phenyl selenide.
    Notes: 29-tert-Butyldimethylsilyloxy-3,11-dimethyl-1-nonacosen (17) wird durch Grignardkupplung von p-Tolyl-(S)-24-tert-butyldimethylsilyloxy-6-methyl-1-tetracosansulfonat (15) mit 5-Brom-3-methyl-1-penten (16) synthetisiert. Das Tosylat 15 ist aus (S)-24-Hydroxy-6-methyltetracosansäure-methylester (11) durch Schutz der freien Hydroxylgruppe und Reduktion der Esterfunktion mit anschließender Tosylierung erhältlich. Der Ester 11 wird durch doppelte Kolbe-Elektrolyse von 18-Hydroxyoctadecansäure (5) mit (S)-3-Methylglutarsäure-monomethylester (6) und an-schließend mit Glutarsäure-monomethylester (9) aufgebaut. Das Bromid 16 wird ebenfalls aus dem Halbester 6 durch Reduktion der Esterfunktion und Phenylselenid-Eliminierung synthetisiert.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820812
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  • 5
    Electronic Resource
    Electronic Resource
    Regioselektive Funktionalisierung nicht aktivierter CH-Bindungen, 3. Synthese und Eigenschaften photoreaktiver, amphiphiler Benzophenonderivate (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 589-596 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Regioselective Functionalization of Nonactivated CH-Bonds, 3. - Synthesis and Properties of Photoreactive, Amphiphilic Benzophenone CompoundsThree differently substituted benzophenone-4-carboxylic acids 1e, 1g, 1h and myristic acid (2a), representing anionic, single-chain amphiphiles, and esters of 1e and 2a with quaternized β-amino alcohols as examples of single-chain (11, 2e) and double-chain (3b, 3c, 3d, 3e) cationic amphiphiles were examined with regard to their aggregation behaviour in aqueous solution. While the single-chain amphiphiles showed ideal miscibility in micellar solution, separation was observed for the double-chain amphiphiles 3b and 3e in bilayers. Amphiphiles with benzophenone segments, compared to those with only alkyl chains (3e), lead to a lowered phase transition temperature, the formation of smaller or less stable vesicles, or a complete prevention of vesicle formation.
    Notes: Drei unterschiedlich substituierte Benzophenon-4-carbonsäuren 1e, 1g, 1h und Myristinsäure (2a) als anionische, einkettige Amphiphile sowie Ester von 1e und 2a mit quartären β-Aminoalkoholen als Vertreter einkettiger (11, 2e) und zweikettiger (3b, 3c, 3d, 3e) kationischer Amphiphile wurden auf ihre Aggregatbildung in wäßriger Lösung untersucht. Während die einkettigen Amphiphile in micellarer Lösung ideale Mischbarkeit zeigen, wird im Falle der zweikettigen Amphiphile 3b und 3e in Doppelschichtaggregaten Entmischung beobachtet. Amphiphile mit Benzophenonsegmenten führen gegenüber solchen mit reinen Alkylketten (3e) zur Senkung der Phasenumwandlungstemperatur, der Bildung kleinerer oder weniger stabiler Vesikel oder verhindern völlig die Vesikelbildung.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870705
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  • 6
    Electronic Resource
    Electronic Resource
    Pheromone, 57. Synthese Methylen-unterbrochener Lepidopteren-Polyenpheromone und Strukturanaloger. Acetylensynthese, Wittig-Reaktion und Kolbe-Elektrolyse (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 417-422 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Pheromones, 57. - Synthesis of Lepidoptera Polyene Pheromones and of Structural Analogs. - Acetylenic Synthesis, Wittig Olefination, and Kolbe ElectrolysisBy a combination of acetylenic syntheses with Wittig olefination as well as by mixed Kolbe electrolysis alkadienes, alkatrienes, and alkatetraenes (sex attractants of Lepidoptera and structural analogs) were synthesized.
    Notes: Durch Kombination von Acetylensynthesen und Wittig-Olefinierung sowie durch gemischte Kolbe-Elektrolyse werden Methylenunterbrochene Alkadiene, Alkatriene und Alkatetraene (Sexuallockstoffe von Lepidopteren und Strukturanaloge) synthetisiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870346
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  • 7
    Electronic Resource
    Electronic Resource
    Anodische Oxidation von Arylolefinen (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 204-224 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Anodic Oxidation of Aryl OlefinsFour styrene derivatives and indene are oxidatively dimerized in an undivided cell at a graphite anode in methanol/sodium perchlorate or methanol/sodium camphorsulfonate to form 1,4-dimethoxy-1,4-diphenylbutane or 1-4-diphenylbutadiene derivatives, respectively, in up to 80% yield. In some cases product distribution is strongly dependent on the anode potential and the supporting electrolyte. β-Alkyl substituents drastically lower the dimer yield (1-cyclopentenylbenzene) or favor the formation of dimethoxylated monomers (indene). The aryl olefins are irreversibly oxidized at peak potentials between Ep = +0.63 and +1.68 V (vs. Ag/AgCl) with n-values of about 2 at the limiting current; the peak potentials of p-substituted styrenes correlate linearly with their σp+-values. The dimers are probably formed via radical cations that add as electrophiles to the aryl olefin with formation of a 1,4-radical cation which, after oxidation, undergoes solvolysis of deprotonation.
    Notes: Vier Styrolderivate und Inden werden in einer ungeteilten Zelle an einer Graphitanode in Methanol/Natriumperchlorat und Methanol/Natriumcamphersulfonat in Ausbeuten bis 80% zu 1,4-Dimethoxy-1,4-diphenylbutan- bzw. 1,4-Diphenylbutadienderivaten dimerisiert, deren Produktanteil zum Teil entscheidend durch Anodenpotential und Leitsalz bestimmt wird. β-Alkylsubstituenten vermindern drastisch die Dimerenausbeute (1-Cyclopentenlbenzol) oder begünstigen die Bildung dimethoxylierter Monomere (Inden). Die untersuchten Arylolefine werden irreversibel bei Peakpotentialen zwischen Ep = +0.63 und + 1.68 V (gegen Ag/AgCl) mit n-Werten um 2 im Grenzstrombereich oxidiert; die Peakpotentiale p-substituierter Styrole korrelieren linear mit deren σp+-Werten. Die Dimeren bilden sich vermutlich über Radikalkationen, die sich elektrophil an das Arylolefin zu einem 1,4-Radikalkation, addieren, das oxidiert und anschließend methanolysiert oder deprotoniert wird.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719770203
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  • 8
    Electronic Resource
    Electronic Resource
    Diastereoselektive Kupplung anodisch erzeugter Radikale mit chiralen AmidgruppenProfessor Wolfgang Lüttke zum 75. Geburtstag gewidmetElektroorganische Synthese, 60. Mitteilung. Diese Arbeit wurde vom Fonds der Chemischen Industrie und vom EC Human Capital and Mobility Programme (Nr. ERBCHRXCT 920073) gefördert. - 59. Mitteilung: C. Zielinski, H. J. Schäfer, Tetrahedron Lett. 1994, 35, 5621-5624. (1995)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 107 (1995), S. 218-220 
    Details
    ISSN: 0044-8249
    Keywords: Asymmetrische Synthesen ; Auxiliare ; Kolbe-Elektrolyse ; Radikale ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19951070217
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  • 9
    Electronic Resource
    Electronic Resource
    Electroorganic Synthesis, 54. Enantioselective Cathodic Reduction of 4-Substituted Coumarins with Alkaloids as Catalysts, 1Dedicated to Professor Dr. Ulrich Schöllkopf on the occasion of his 65th birthday. (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 601-607 
    Details
    ISSN: 0170-2041
    Keywords: Electrochemistry ; Coumarins, reduction of ; Enantioselective protonation ; Alkaloids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The optical yield in the alkaloid-catalyzed enantioselective electroreduction of 4-methylcoumarin (1a) was increased from 17% to 47.4% by systematic variation of the electrolysis conditions. The results are explained by an induction mechanism in which the adsorbed protonated alkaloid acts as a chiral proton donor towards a prochiral carbanion derived from 1a. The preferred configuration of the product and the results obtained by variation of the alkaloid structure allow us to propose a model of the transition state. Furthermore, 4-phenylcoumarin (1b) and 4-(trifluoromethyl)coumarin (1c) were reduced with 13.2% and 8.4% ee, respectively.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930198
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  • 10
    Electronic Resource
    Electronic Resource
    Conversion of Fatty Acids and Derivatives, IV. Conversion of Fatty Acid Methyl Esters into Dialkylated Succinic Esters by Oxidative Coupling of their Enolates (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1219-1223 
    Details
    ISSN: 0170-2041
    Keywords: Fatty acid methyl esters ; Enolates ; Oxidative coupling ; Succinic acid diesters ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enolates of fatty acid methyl esters 1a-g are dimerized in good yields (56 to 73%) by means of oxidative coupling with copper(II) bromide to dialkylated succinic esters 2a-g. The configuration of meso-2a was established by independent synthesis. On treatment with ozone the unsaturated dimer 2c is converted to the tetracarboxyl compound 6. Epoxidation of 2g leads to the corresponding bisepoxy diester 7.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301197
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