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  • Organic Chemistry  (2)
  • Hydride shift
  • Phenylmethylium
  • Wiley-Blackwell  (2)
  • 1985-1989  (2)
  • 1985  (2)
Collection
Keywords
Publisher
  • Wiley-Blackwell  (2)
Years
  • 1985-1989  (2)
Year
  • 1
    Electronic Resource
    Electronic Resource
    Zur sukzessiven Umhüllung des Benzolkerns mit gesättigten Ringen (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 226-238 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Successive Enveloping of the Benzene Nucleus with Saturated RingsStarting with benzosuberone (3) the tri- up to hexacyclic ketones 4-7 are prepared by successive annulations, requiring three single steps in each case, 1) carbonyl olefination to yield the unsaturated esters 9, 13, 15, and 17, 2) reduction with NaBH4/NiCl2 to give the corresponding saturated esters (or acids, respectively) 11, 14, 16, and 18, and 3) cyclization with trifluoroacetic acid/trifluoroacetic anhydride. Concluding reactions of the sterically unresolved hexacyclic ketone 7 with methylenetriphenylphosphorane yield the exomethylene derivative 19 as mixtures of diastereomers with varying composition. Attemps to the final cyclization and dehydrogenation of 19 produced only tar- and coal-like materials.
    Notes: Ausgehend von Benzosuberon (3) werden durch sukzessive Anellierung die tri- bis hexacyclischen Ketone 4-7 hergestellt, wobei jeweils drei Einzelschritte benötigt werden. 1) Carbonyl-Olefinierung zu den ungesättigten Estern 9, 13, 15 und 17, 2) Reduktion mit NaBH4/NiCl2 zu den entsprechenden gesättigten Estern (bzw. Säuren) 11, 14, 16 und 18 sowie 3) Cyclisierung mit Trifluoressigsäure/Trifluoressigsäureanhydrid. Anschließende Umsetzungen des sterisch uneinheitlichen hexacyclischen Ketons 7 mit Methylentriphenylphosphoran führen zum Exomethylen-Derivat 19 in Form von Diastereomeren-Gemischen wechselnder Zusammensetzung. Versuche zur endgültigen Cyclisierung und Dehydrierung von 19 lieferten lediglich Teer- oder Kohle-artige Produkte.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850203
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  • 2
    Electronic Resource
    Electronic Resource
    Eine allgemeine Synthesemethode für Dibenzo[b,j][x,z]phenanthroline mit x,z = 1,7; 4,7 und 1,10 (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1501-1507 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A General Synthetic Method for Dibenzo[b,j][x,z]phenanthrolines with x,z = 1,7; 4,7, and 1,10When 2-aminoacetophenone (1) and 2-aminobenzophenone (4) are reacted with 1,3-, 1,2-, or 1,4-diiodobenzene, dibenzophenanthrolines 2, 6, 8, and 10 with fusion patterns [b,j][1,7]; [b,j][1,10], and [b,j][4,7], respectively, are obtained either directly or after acid-catalyzed cyclization of the primarily isolated intermediates 3, 4, 7, and 9.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850722
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    Paper (German National Licenses)
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