REACTION OF N,N-DICHLOROETHANESULFONAMIDE WITH 1-OLEFIN

The competitive ionic and radical reactions of N,N-dichloroethanesulfonamide and 1-olefins yielded two isomers of the 1:1 adduct under the normal indoor lighting, but the predominant formation of the anti-Markownikoff adduct was observed under photoirradiation. By photoirradiation of the products obtained in the reaction under the normal indoor lighting, two corresponding rearranged products were obtained. These 1:1 adducts and rearranged products were converted to N-ethanesulfonylaziridine derivatives by alkali treatment. A mechanism for the participation of N-monochloroethanesulfonamide has been proposed. © 1969.