Lewis acid mediated elimination and rearrangement reactions of α-chlorosulfides derived from phenylthio-substituted 4,5-dihydrofuran-3(2H)-ones.

Abstract

Phenylthio-substituted 4,5-dihydrofuran-3(2H)-ones were converted into α-chlorosulfides in a highly diastereoselective manner with sulfuryl chloride. Treatment of the chlorides with stoichiometric amounts of Lewis acids gave furan-3(2H)-one products resulting from elimination and aryl group migrations. Similar behaviour was observed with an α-acetoxy sulfide derivative. The X-ray crystal structures of a representative α-chlorosulfide and of a novel, ring sulfenylated product were determined.