Preparation and Synthetic Applications of (Dimethylamino)phenyloxosulfonium Methylide

Abstract

The preparations of N,S-dimethyl S-phenyl sulfoximine and its N-methylated salt—(dimethylamino)methylphenyloxosulfonium fluoroborate—are described. These materials represent classes of compounds not previously reported. Treatment of the above salt with sodium hydride in a variety of solvents generated the title ylide. The ylide has been shown to react with aldehydes and ketones to produce oxiranes, with electrophilic olefins to yield cyclopropanes, with benzalaniline to produce 1,2-diphenylaziridine, and with benzoyl chloride and phenyl isocyanate to produce carbonyl-stabilized ylides. In the nucleophilic methylene transfer reactions the byproduct is N,N-dimethylbenzenesulfinamide. © 1970, American Chemical Society. All rights reserved.