A 1,3-rearrangement of allylic sulphones caused by m-chloroperbenzoic acid and sodium hydrogen carbonate

Abstract

The reaction of allylic sulphones with m-chloroperbenzoic in the presence of aqueous sodium hydrogen carbonate can result in 1,3-allylic rearrangement or isomerisation of the double bond depending on the structure of the allylic sulphone. Subsequent epoxidation then gives β,γ-epoxy-sulphones. Epoxidation of allylic sulphones in the absence of sodium hydrogen carbonate gives, β-γ-epoxy-sulphones in which the position and stereochemistry of the double bond is retained. A radical-chain mechanism is proposed for the rearrangement reactions.