The Chlorination of O-Ethyl N-(1-Tosylalkyl)Thiocarbamates and Ethyl N-(1-Tosylalkyl)Dithiocarbamates

Abstract

In a previous paper¹ it was reported that S-ethyl N-(1-tosylalkyl) thiocarbamates react with chlorine in a heterogeneous mixture of dichloromethane and aqueous sodium hydrogen carbonate to give 1-tosylalkyl isocyanates, presumably via intermediate N-(1-tosylalkyl)carbamoyl chlorides. The corresponding reaction with bromine followed a similar course. In view of these results and since little is known^2–5 about the reactions of thiocarbonyl compounds with halogens, we have investigated the reactions of the readily accessible⁶ O-ethyl N-(1-tosylalkyl)thiocarbamates and ethyl N-(1-tosylalkyl)dithiocarbamates with anhydrous chlorine.