The Journal of Organic Chemistry

Reactions of unsaturated sulfides with carbenes. 22. Reactivities of sulfur and double bond, and formation of unsaturated sulfonium ylides

W Ando, H Higuchi, T Migita

Index: Ando,W. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 21 p. 3365 - 3372

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Citation Number: 21

Abstract

The reaction of vinyl sulfides with carbomethoxycarbene leads to the formation of methyl vinylthioacetate as major product and some cyclopropane adduct as minor product. The reaction of vinyl sulfides with biscarbomethoxycarbene leads to the corresponding stable sulfonium ylide which decomposed thermally to vinylthiomalonate. The NMR spectra of vinyl sulfides and vinyl sulfonium biscarbomethoxymethylide are discussed. Although the ...