Preparation and Reactions of Sulfonimidoyl Fluorides

Abstract

Sulfonimidoyl fluorides have been prepared for the first time by treatment of sulfonimidoyl chlorides with various sources of fluoride ion. Sulfonimidoyl chlorides are reduced to sulfinamides with alkyllithium reagents; however, the corresponding fluorides are converted in high yield to sulfoximines upon treatment with primary alkyllithiums. In the presence of Lewis acids, N-methylbenzenesulfonimidoyl fluoride was shown to react with anisóle in a Friedel-Crafts manner and with silyl enol ethers to produce β-keto sulfoximines. © 1983, American Chemical Society. All rights reserved.