Cyclization of N-2-chloroalkyl-p-chlorobenzenesulfonamides to azirindes

Abstract

1. The adducts of N,N-dichloro-p-chlorobenzenesulfonamide with ethylene and vinyl chloride were synthesized. 2. The alkaline cyclization of the adducts of N,N-dichloro-p-chlorobenzenesulfonamide with ethylene, styrene, allyl chloride and acrylonitrile gave the corresponding aziridines. 3. The cyclization of the adducts, with the cleavage of chlorine from either the 2,2-chloro or the 2,2,2-trichloromethyl group, fails to go under the influence of alkali, probably due to the high shielding of the carbon atom in the indicated groups against nucleophilic attack.