Abstract
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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References
Sontag, D., Ann. Chim. (11), 1 (1934).
Wallace, T. J., Pobiner, H., Hofmann, J. E., and Schriesheim, A., Proc. Chem. Soc., 673 (1963).
Price, C. C., and Oae, S., Sulfur Bonding (Ronald Press, New York, 1962).
Parker, A. J., Quart. Rev., 16, 163 (1962).
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WALLACE, T., HOFMANN, J. & SCHRIESHEIM, A. Characteristics of Benzylic Carbanions. Nature 199, 1287–1288 (1963). https://doi.org/10.1038/1991287b0
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DOI: https://doi.org/10.1038/1991287b0
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