Reactions of sulfonhydrazides with benzeneseleninic acid, selenium halides, and sulfur halides. A convenient preparation of selenosulfonates and thiosulfonates

The oxidation of sulfonhydrazides with benzeneseleninic acid provides an efficient and convenient preparation of selenosulfonates. Se-Phenyl p-tolueneselenosulfonate was also produced in good to excellent yield from the reaction of p-toluenesulfonhydrazide with PhSeCl, PhSeBr3, or PhSeCl3. Sulfonhydrazides react with sulfenyl halides or with PhSBr3 to produce thiosulfonates in generally high yield. The treatment of p-toluenesulfonhydrazide with benzenetellurinic acid, PhTeCl3, or PhTeBr3 afforded only diphenyl ditelluride and not the corresponding tellurosulfonate.