Reactions of N-chloramines and N-haloamides with unsaturated compounds

The results obtained from studying the reactions of N-chloramines, N-halocarbamates, and N-haloamides of carboxylic, sulphonic, and phosphoric acids with unsaturated compounds have been correlated and classified. It is shown that the direction of addition of N-haloamines and N-haloamides to alkenes, dienes, alkenynes, and acetylenes, giving saturated adducts, is determined by the conditions of homolytic or heterolytic initiation. The reactions of N-chlorodialkylamines with olefins in the presence of sulphur trioxide are discussed. A new method of activating electrophilic reagents by introducing sulphur trioxide on to the N–Cl bond is identified.
An essentially new trend is reported for the reactions of N,N-dihaloamides of sulphonic and carboxylic acids and also N,N-dihalocarbamates with polyhaloethylenes, giving acylimines of polyhaloaldehydes, which are highly reactive syntones for the synthesis of fine organic chemicals.
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