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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 713-721 
    ISSN: 1434-193X
    Keywords: Reductive alkylation ; Acenaphthylenes ; Carbanions ; Polycycles ; Single-electron transfer ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---Reaction of the 5-hydroacenaphthylene anion with benzyl halides proceeds at carbon atom 1 as well as at carbon atom 2a, in the latter case creating a quaternary centre. The hardness-softness of the electrophiles was shown to play only a minor role in determining the regioselectivity of the reaction of the hydroanion with several benzyl and alkyl halides: the leaving group hardly affects the ratio of 1- and 2a-substituted products. This indicates that the alkylation might proceed by an electron transfer (SET) instead of an SN2 mechanism. Further evidence for SET was obtained by the use of free radical and electron scavengers. The substitution products 1-benzylacenaphthene and 2a-benzyl-2a,5-dihydroacenaphthylene could be isolated and purified.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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