Synthesis of cyclic allylic sulphides (ring sizes 5–15)via phenylthio participation

Abstract

Dehydration of β-phenylthio alcohols occurs with PhS participation unless stereochemistry prevents it. Without PhS participation, mixtures of allylic and vinylic sulphides are formed, but with PhS participation routes to three families of cyclic allylic sulphides (9), (13), and (14)(n= 5, 6, 7, 8, 10, 12, or 15) can be chosen. 2-exo-Methylenecycloalkanols were made from (14).