α,β-Epoxy sulfoxides and sulfones. Synthesis and some reactions

Abstract

A number of α,β-epoxy sulfoxides and epoxy sulfones have been prepared via cyclization of α-chloro-β-hydroxy sulfoxides or phase-transfer catalyzed reaction between α-chloroalkyl sulfones and carbonyl compounds. Thermal and acid-catalyzed rearrangement of these epoxides resulted in migration of sulfinyl or sulfonyl groups to form β-carbonyl sulfoxides or sulfones. Upon treatment of the epoxy sulfones with MgBr2 in ether, α-bromocarbonyl compounds were obtained in excellent yield. The reaction of epoxy sulfones with nucleophiles was also briefly investigated.