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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1907-1914 
    ISSN: 1434-193X
    Keywords: Reductive alkylation ; Acenaphthylene ; Carbanions ; Polycycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The dianion of acenaphthylene can be converted into the 5-hydroanion by protonation with one equivalent of methanol. Subsequent reaction with electrophiles such as allyl bromide and propargyl bromide occurs selectively at position 1, resulting in the formation of the novel 1-allylacenaphthene and 1-propargylacenaphthene. In addition to what was observed in the case of methyl iodide, the hitherto unknown 1,1-dialkylated acenaphthene derivatives are formed as minor products; probably the lower reactivity of the unsaturated bromides is responsible for this side reaction. From the products of the reactions with 3,3-dimethylallyl bromide and (bromomethyl)cyclopropane the mechanism was found to be SN2. Reaction of the hydroanion with benzyl bromide takes place at position 1 as well as at position 2a. The reactivity of carbon 2a towards the soft electrophile benzyl bromide is attributed to the high HOMO coefficient at this position.
    Type of Medium: Electronic Resource
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