Allyl sulphide synthesis by phenylthio migration: relationship between stereochemistry of starting materials and regioselectivity of double bond formation

Abstract

Phenylthio migration to an alkyl migration terminus can be controlled to give mostly an allyl sulphide with a trisubstituted double bond and good E : Z selectivity but migration to a benzylic migration terminus is affected by stereochemistry: each diastereoisomer of the starting material preferentially forms one of two regioisomeric allylic sulphides.