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Mechanism and Method for Synthesis of Sulfides by Thiol-disulfide Exchange Reaction

[ Vol. 11 , Issue. 2 ]


Rong Lu, Saori Itabashi, Naoki Enjo and Tetsuo Miyakoshi   Pages 295 - 300 ( 6 )


A series of sulfides was 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 has been 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.

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