Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines

The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceded in the presence of a copper catalyst. The procedure was performed efficiently in air, and afforded the corresponding sulfenamides. (C) 2017 Elsevier Ltd. All rights reserved.