1,3-Acyl migration in carbonic acid derivatives—synthesis of S-polyhalogenoalkyl N-acyl-N-aryl(alkyl)thiocarbamates

Abstract

Aryl(alkyl)iminochloromethyl polyhalogenoalkyl sulphides react with carboxylic acids to give S-polyhalogenoalkyl N-acyl-N-aryl(alkyl)thiocarbamates, which have not been synthesized by other routes. By analogy with known 1,3 rearrangements, the reaction appears to involve a nucleophilic substitution followed by a new type of 1,3-acyl migration. Similarly, with sodium azide 1-methyl- and 1-phenyl-5-trichloromethylthiotetrazoles are also obtained.