Scope and limitations of allyl sulphide synthesis by [1,2] and [1,3] phenylthio migration

Abstract

β-Phenylthio-alcohols rearrange in acidic solution (toluene-p-sulphonic acid in benzene under reflux) to give allyl sulphides by phenylthio migration. High yields of single products useful in organic synthesis are obtained with a tertiary or secondary migration origin and a primary migration terminus providing that a branched chain is not present at the migration origin. Attempts to control the regioselectivity of reactions of allyl sulphide anions are described: only cadmium(II) iodide gave a high yield of a single product.