Homolytic displacement at carbon centres: XII. Regiospecific formation of N-allyl and N-cyclopropylcarbinyl sulphonamides and of allyl and cyclopropyl halides in the reaction of N-halogeno compounds with organocobaloximes

Several but-3-enyl and allylcobaloximes react regiospecifically with N-chloro-N-methyl sulphonamides to give N-cyclopopylcarbinyl- or rearranged N-allyl-N-methyl sulphonamides, by a process which is believed to take place by the attack of an N-centred radical at the terminal unsaturated carbon of the organic ligand, with displacement of cobaloxime(II). In contrast, N-bromoacetamide and several other N-halogenoimides react regiospecifically to give the cyclopropylcarbinyl halide or the rearranged allyl halide by a process in which a halogen-containing free radical species attacks the terminal unsaturated carbon of the organocobaloxime.