Tetrahedron

Preparation of nitramine-nitrates by ring-opening nitration of azetidines by dinitrogen pentoxide (N 2 O 5)

P Golding, RW Millar, NC Paul, DH Richards

Index: Golding, Peter; Millar, Ross W.; Paul, Norman C.; Richards, David H. Tetrahedron, 1995 , vol. 51, # 17 p. 5073 - 5082

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Citation Number: 22

Abstract

Eleven azetidines, bearing various types of substituents on the ring nitrogen, were treated with N2O5 in chlorinated solvents at sub-ambient temperature and in certain cases formed 1, 3-nitramine-nitrate products by a novel ring-opening nitration reaction analogous to that established for aziridines. Yields of the nitramine-nitrates, where ring-opening took place, were generally moderate to high (41–88%), but azetidines bearing N-acyl substituents ( ...