Preparation of di-and polynitrates by ring-opening nitration of oxetanes by dinitrogen pentoxide (N 2 O 5)

P Golding, RW Millar, NC Paul, DH Richards

Index: Golding; Millar; Paul; Richards Tetrahedron, 1993 , vol. 49, # 32 p. 7051 - 7062

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Citation Number: 23

Abstract

Ten oxetanes bearing various substituents were reacted with N2O5 in chlorinated hydrocarbon solvents to yield 1, 3-dinitrate esters (I) by ring-opening nitration. The yields ranged from 73 to 88% for di-/trinitrates derived from oxetanes unsubstituted in the 2- position, to only 15 to 21% for oxetanes bearing such substituents. Although selective ring cleavage of oxetanes bearing non-hydroxylic substituents (epoxy (oxiranyl), spiro-oxetane ...