Decomposition of a series of N-chloro amides in solution has been examined as a function of the solvent, the structure of the N-chloro amide, the mode of initiation, and the effect of additives. The reactions proceed by freeradical chain decomposition, affording products derived from intra-and intermolecular hydrogen abstraction. The light-initiated decompositions of N-chloro-N-methylacetamide (la), N-chloro-N-tert-butylacetamide (2a), ...