Chlorination of oximes in hydrogen fluoride: formation of gem-dihalogenoalkanes

Article abstract of DOI:10.1016/0022-1139(94)03119-K

The action of chlorine on oximes in hydrogen fluoride as a medium gives gem-dihalogenoalkanes.The reaction proceeds through the intermediate formation of gem-chloronitrosoalkanes.The relative proportions between gem-dichloro, -difluoro and -fluorochloro compounds are dependent on the presence of a cosolvent.The use of other oxidants, such as nitric oxide, dinitrogen tetroxide or nitrosyl chloride, gives similar compounds: - Keywords: Chlorination, Oximes; Hydrogen fluoride; Dihalogenoalkanes; NMR spectroscopy, Mass spectrometry