The formation of nitrimines, by the action of nitrous acid on oximes, is shown to proceed without scrambling of the nitrogen atoms, the oxime nitrogen forming the imine, and the nitrous acid generating the nitro group. Coloured intermediates in the reaction are proposed to be nitrosimines. The mechanism of nitrosative deoximation, and the nitrogen n.m.r. spectra of nitrimines, are reported and discussed.
138ChemInform Abstract The formation of nitrimines, by the action of nitrous acid on oximes, is shown to proceed without scrambling of the nitrogen atoms, the oxime nitrogen forming the imine, and the nitrous acid generating the nitro group. Colored intermediates in the reaction are proposed to be nitrosimines. The mechanism of nitrosative deoximation, and the nitrogen NMR spectra of nitrimines are reported and discussed. Nitrimines considered in the investigation are, for example, the compounds (IV), (VI)-(IX). The preparation of (IV) and (VI) is given, whereas (VII)-(IX) are prepared following known procedures. Furthermore, labeled analogues corresponding to (IV), (VI), (VII) which are prepared using 15N-enriched HNO2 are studied.
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