Synthesis of cyclic sulfides using phenylthio migration

Article abstract of DOI:10.1016/0040-4039(95)02248-1

New routes to cyclic and spirocyclic sulfides involve aldol reactions of dithioesters or chemoselective Mitsunobu reactions on diols to give 2-hydroxyalkyl sulfides with a terminal SH group. Treatment with acid gives cyclic sulfides, or by rearrangement with S migration, spirocyclic sulfides or allylic sulfides in good yield.