Activation of Weak Organic Bases. III. The Reactions of Divalent Sulfides with Acid Chlorides in the Presence of Friedel-Crafts Catalysts

Abstract

The reaction of thioanisol with acetyl chloride in the presence of SbCl₅ was attempted hoping the isolation of acetylsulfonium cation (V). The product actually obtained was found to be the sulfonium ion (IXa), which was also isolated from thioanisol and SbCl₅ without using acetyl chloride. The same type of compounds (IXb, XII, and XIV) was obtained in an analogous fashion. The mechanism of these reaction has been discussed. When dialkyl sulfides were treated with benzoyl chloride in the presence of AgClO₄, the expected benzoyldialkylsulfonium ions were isolated. The reaction of these salts with nucleophiles has also been described.