The Reaction of Sulfilimine with Phenyl Grignard Reagent

Abstract

Abstract The reactions of diphenyl (I), phenyl benzyl (II), and phenyl methyl N-p-tosylsulfilimines (III) with phenylmagnesium bromide were carried out. (I) gave biphenyl and diphenyl sulfide in high yields. A tracer experiment with diphenyl sulfilimine-1-14C revealed that the reaction proceeds via the initial formation of triphenylsulfonium salt upon which the attack of phenylmagnesium bromide affords the products. “Benzyne” mechanism is ruled out. (II) and (III) gave various compounds, the major products being α-phenylated sulfides which are presumed to be formed by the Pummerer type rearrangement initiated by the abstraction of α-proton by the Grignard reagent.