CHEMISTRY OF NITROGEN RADICALS .9. REACTIONS OF N-HALOCYANAMIDES AND N-HALOSULFONAMIDES

The photolytic rearrangement of N-t-butyl-N-halobutanesulfonamides to the corresponding 3-halobutane-sulfonamides occurred in ~75% yield; cyclization of the products gave either the sultam (V) by ring closure at nitrogen or an isomeric cyelopropanesulfonamide (IV) by ring closure at the carbon α to the sulfone group. Additions of N-chloro-N-methylcyanamide and N-chloro-N-methylmethanesulfonamide to both conjugated and nonconjugated olefins in 45-75% yield are also reported. Photolytic reactions of N-t-butyl-N-chloro-cyanamide in the presence of olefins gave carbodiimide derivatives as the principal products. © 1969, American Chemical Society. All rights reserved.