Tetrahedron

Rearrangement of carbanions and of ylides derived from 4-thiacyclohexenyl systems

JF Biellmann, JB Ducep, JJ Vicens

Index: Biellmann,J.F. et al. Tetrahedron, 1976 , vol. 32, p. 1801 - 1805

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Citation Number: 22

Abstract

The rearrangement of the carbanion and of the ylide derived from 5, 5-diphenyl-4- thiacyclohexene to (E) 2, 2-diphenyle-1-methylthiovynylcyclopropane is shown to depend on the presence of a stabilizing substituent at C-5. A non concerted mechanism is proposed for this rearrangement. The carbanions from the 4-thiacyclohexene and from the sulfone of the 5, 5-diphenyl-4-thiacyclohexene are stable. The cycloaddition of an aromatic ...