A New Procedure for the Conversion of Thiols into Reactive Sulfenylating Agents

Article abstract of DOI:10.1021/jo00023a039

Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3.Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with β-diketones to afford sulfides.This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise r eactive thiols.