Mechanism and Method for Synthesis of Sulfides by Thiol-disulfide Exchange Reaction
Rong Lu, Saori Itabashi, Naoki Enjo and Tetsuo Miyakoshi
A series of sulfides were successfully synthesized by a thiol-disulfide exchange reaction using disulfides as the reactive substance. After cleavage of S-S bonds by ammonium thioglycolate catalysis, Michael addition reactions were performed using various acceptors in one-pot. The catalyzed-reaction mechanism is discussed based on the by-products. In addition, 2,3H-1,5-benzothiazepines were also successfully synthesized from 2,3H-1,5-benzothiazepine-4(5H)-one with satisfactory yields using Lawesson’s reagent.
Ammonium thioglycolate, benzothiazepine, sulfide, synthesis
Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashi-mita, Tama-ku, Kawasaki-shi, 214-8571, Japan.