New Synthesis of Alkane-and Arylsulfonyl Chlorides by Oxidation of Thiols and Disulfides with Chlorine Dioxide

摘要

Sulfonyl chlorides are extensively used in the production of detergents, ion-exchange resins, elastomers, pharmaceuticals, dyes, herbicides, as semiproducts in the synthesis of sulfonic acids esters. Industrial and laboratory scale production of sulfonyl chlorides is based on reactions of aliphatic hydrocarbons with sulfuryl halides or with a mixture of sulfur dioxide and chlorine, on the oxidative chlorination of thiols, sulfides, disulfides; on the oxidation of sulfenyl chlorides; on the reaction of sulfonic acids and their derivatives with PC15, COCl2, thionyl chloride, chlorine, and chlorosulfonic acid. Sulfonyl halides form also in reactions of organomagnesium compounds with sulfuryl halide or of diazonium salts with sulfur dioxide and CuCl2 [1]. However all these methods have certain disadvantages due to the severe reaction conditions and side processes.