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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2900-2909 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Assignment of Configuration of Larger Bicyclo[n.1.0]alkyl Amines: The Hexahydro-1-azepinyl Residue as „Stereo Indicator“The temperature dependency of the 1H NMR spectra of the hexahydro-1-azepinylbicyclo[9.1.0]-dodecanes 3a  -  f is investigated. The ΔG≠-values of the hexahydroazepine dynamics permit an easy assignment of the endo-amino configuration in 3a  -  f. Starting from 3a, which is synthesized via the enaminosulfonium salt 7, the derivatives 3b  -  f are obtained by nucleophilic substitutions. Normally the cis-configuration of the bicyclo system is not changed during these reactions. However, reaction of the cis-compound 3a with hexahydroazepine leads either to a cis-aminal 3e or to a trans-aminal 4e depending on the conditions of the reaction.
    Notes: Die aus der Temperaturabhängigkeit der 1H-NMR-Spektren der Hexahydro-1-azepinylbicyclo [9.1.0]dodecan-Derivate 3a  -  f ermittelten ΔG≠-Werte der Hexahydroazepinyl-Dynamik ermöglichen eine einfache Festlegung der endo-Amino-Konfiguration. Die Verbindungen 3b  -  f werden aus 3a über eine Folge nucleophiler Substitutionen erhalten; 3a ist über das Enaminsulfonium-Salz 7 zugänglich. Normalerweise bleibt die cis-Konfiguration des Bicyclosystems bei den Substitutionen erhalten. Jedoch führt die Umsetzung der cis-Verbindung 3a mit Hexahydroazepin  -  abhängig von den Reaktionsbedingungen  -  zu einem cis-Aminal 3e oder einem trans-Aminal 4e.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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