Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole

Roger Hunter; Mino Caira; Nashia Stellenboom

doi:10.1021/jo060693n

Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole

J Org Chem. 2006 Oct 13;71(21):8268-71. doi: 10.1021/jo060693n.

Authors

Roger Hunter¹, Mino Caira, Nashia Stellenboom

Affiliation

¹ Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa. [email protected]

PMID: 17025323
DOI: 10.1021/jo060693n

Abstract

A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at -78 degrees 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azoles / chemistry
Chlorobenzenes / chemistry
Disulfides / chemical synthesis*
Sulfhydryl Compounds / chemistry

Substances

Azoles
Chlorobenzenes
Disulfides
Sulfhydryl Compounds