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

ISSN: 1875-6271 (Online)
ISSN: 1570-1794 (Print)

Volume 12, 6 Issues, 2015

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Current Organic Synthesis

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Eduardo A. Castro
Universidad Nacional de La Plata
Buenos Aires

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Current: 2.117
5 - Year: 2.425

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

Current Organic Synthesis, 11(2): 295-300.

Author(s): Rong Lu, Saori Itabashi, Naoki Enjo and Tetsuo Miyakoshi.

Affiliation: Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashi-mita, Tama-ku, Kawasaki-shi, 214-8571, Japan.


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.

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Article Details

Volume: 11
Issue Number: 2
First Page: 295
Last Page: 300
Page Count: 6
DOI: 10.2174/1570179411666140123234712

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