The Mechanism of the Alkaline Decomposition of Triarylsulfonium Bromide with Phenyllithium

Abstract

Abstract Tritolylsulfonium bromide was subjected to alkaline decomposition in order to clarify the mechanism of the reaction of triarylsulfonium bromide with phenyllithium in ether. Diaryl sulfides, diaryls, and other aryl derivatives were obtained and the combined yield was nearly quantitative. On the basis of the ratio of the products formed in the reaction, the alkaline decomposition is considered to proceed through two mechanistic routes, i. e., one involving the nucleophilic attack of phenyl anion on the sulfur atom (about 70%) and the other the “benzyne” route (about 20%).