Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole.
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.
Hunter
Roger
R
Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa. roger@science.uct.ac.za
Caira
Mino
M
Stellenboom
Nashia
N
D001393:Azoles / Q000737:chemistry; D002722:Chlorobenzenes / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry
D001393:Azoles; D002722:Chlorobenzenes; D004220:Disulfides; D013438:Sulfhydryl Compounds