PREPARATION AND REACTIONS OF N-(PARA-TOLYLSULFONYL)SULFILIMINES

N-(p-Tolylsulfonyl)sulfilimines are prepared in high yield by a phase-transfer-catalyzed process fromsolid Chloramine-T trihydrate to a solution of a sulfide in dichloromethane. -Lithio derivatives of N-(p-tolylsulfonyl)- sulfilimines are shown to be useful nucleophilic alkylidene transfer reagents for the conversion of aldehydes and ketones to oxiranes. In the case of benzalacetophenone, 1, 2 addition occurred to yield the oxirane. The facile [2, 3] sigmatropic rearrangement of allylic sulfilimines to sulfinamides is noted. © 1979, American Chemical Society. All rights reserved.