Journal of organometallic chemistry

A convenient preparation of mono-or gem-di-halogenoalkenes from α-sulfonyl carbanions and halogenolithiocarbenoïds

P Charreau, M Julia, JN Verpeaux

Index: Charreau, Philippe; Julia, Marc; Verpeaux, Jean-Noel Journal of Organometallic Chemistry, 1989 , vol. 379, p. 201 - 210

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Citation Number: 28

Abstract

Abstract Various α-sulfonyl carbanions have been shown to react at low temperature with di- or tri-halogenolithiocarbenoïds, to give 1-mono-or 1, 1-di-halogenoalkenes. Bromocarbenoïds gave better results than their chloro-analogues. Reaction of di- bromolithiomethane with α-lithiated sulfones gives a high yield of vinylic bromides, the stereochemistry of which is cleanly E. Evidence is presented that the carbenoïd itself is ...