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28 papers
Reactions of N-chloramines and N-haloamides with unsaturated compounds
A. N. Mirskova,
T. I. Drozdova,
G. G. Levkovskaya,
M. G. Voronkov Irkutsk Institute of Chemistry, Siberian Branch of the USSR Academy of Sciences
Abstract:
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.
The bibliography includes 216 references.
UDC:
547.22'333/298.1/269.352.2+547.31+541.124/6
DOI:
10.1070/RC1989v058n03ABEH003438