Preparation of episulphides from alkenes via succinimide-N-sulphenyl chloride or phthalimide-N-sulphenyl chloride adducts

Abstract

Succinimide- and phthalimide-sulphenyl chlorides are formed in high yield from the corresponding disulphides by chlorinolysis at 50 °C. These imido-sulphenyl halides react in methylene chloride with cyclohexene, cyclopentene, cyclo-octene, styrene, methylenecyclohexane, and norbornene to form addition products which can subsequently be reduced with lithium aluminium hydride at –78 °C to form episulphides in good yield (49–97%). This new method compares very favourably with other literature routes.