Tetrahedron p. 7063 - 7076 (1993)
Update date:2022-08-03
Topics:
Golding, Peter
Millar, Ross W
Paul, Norman C
Richards, David H
Thirteen aziridines, bearing various types of substituents on the ring nitrogen, were treated with N2O5 in chlorinated solvents at sub-ambient temperature and formed 1,2-nitramine-nitrate products by a novel ring-opening nitration reaction analogous to that established for the corresponding oxygen heterocycles (epoxides).A wide variety of classes of aziridine underwent the reaction (N-alkyl, N-(nitroaryl), N-acyl and N-imidyl), the yields in many cases being high (70-82percent), although in one category (the N-(alkylcarbonyl)aziridines) competing deacylation reactions resulted in reduced yields.Also, aziridines bearing groups capable of liberating nitric acid with N2O5 (i.e. those with O-H, N-H or unsubstituted aryl groups) gave rise to greatly reduced yields of the nitramine-nitrates owing to competing rections, principally polymerisation/oligomerisation.
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