Letter | Published:

Characteristics of Benzylic Carbanions

Naturevolume 199pages12871288 (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.

Access optionsAccess options

Rent or Buy article

Get time limited or full article access on ReadCube.


All prices are NET prices.


  1. 1

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

  2. 2

    Wallace, T. J., Pobiner, H., Hofmann, J. E., and Schriesheim, A., Proc. Chem. Soc., 673 (1963).

  3. 3

    Price, C. C., and Oae, S., Sulfur Bonding (Ronald Press, New York, 1962).

  4. 4

    Parker, A. J., Quart. Rev., 16, 163 (1962).

Download references

Author information


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

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


  1. Search for T. J. WALLACE in:

  2. Search for J. E. HOFMANN in:

  3. Search for A. SCHRIESHEIM in:

About this article

Publication history

Issue Date




By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.