Inexpensive, One-Pot Synthesis of Unsymmetrical Disulfides Using 1-Chlorobenzotriazole

Roger Hunter,* Mino Caira, and Nashia Stellenboom
Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa roger@science.uct.ac.za
J. Org. Chem., 2006, 71 (21), pp 8268–8271
DOI: 10.1021/jo060693n
Publication Date (Web): September 15, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at −78 °C in DCM affords a high-yielding conversion to R1SBt without appreciable formation of the symmetrical disulfide R1SSR1. R1SBt is then reacted with R2SH to form the unsymmetrical disulfide in a one-pot sequence with green character that avoids the use of toxic and harsh oxidizing agents. The methodology has been developed for synthesis of various types of disulfides.

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History

  • Published In Issue October 13, 2006
  • Received March 31, 2006

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