Letter | Published:

Characteristics of Benzylic Carbanions

Nature volume 199, pages 12871288 (28 September 1963) | Download Citation



THE formation of a benzylic carbanion from 2-phenylethanethiol in the presence of potassium hydroxide at 200° ultimately yields polystyrene (53 per cent) by a β-elimination of sulphide ion1. Recently, we have observed that the carbanions formed from benzylsulphide and related species in potassium tert-butoxide/dimethylformamide (DMF) at 80° undergo a 1,3-re-arrangement and subsequent β-elimination of the sulphur moiety to yield stilbene2 in the same manner as above. As a logical extension of these studies, we have examined the effect of the hetero atom on rearrangement-elimination reactions of this type. The results obtained are of theoretical rather than synthetic interest.

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  1. 1.

    , Ann. Chim. (11), 1 (1934).

  2. 2.

    , , , and , Proc. Chem. Soc., 673 (1963).

  3. 3.

    , and , Sulfur Bonding (Ronald Press, New York, 1962).

  4. 4.

    , Quart. Rev., 16, 163 (1962).

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  1. Esso Research and Engineering Co., Process Research Division, Exploratory Research Section, Linden, New Jersey.

    • T. J. WALLACE
    • , J. E. HOFMANN


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