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