Tetrahedron

Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N 2 O 5)

RW Millar, SP Philbin

Index: Millar, Ross W.; Philbin, Simon P. Tetrahedron, 1997 , vol. 53, # 12 p. 4371 - 4386

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Citation Number: 39

Abstract

In this novel nitration method dinitrogen pentoxide (N2O5) in an inert solvent is used as the nitrating agent, thereby removing the need for strong acids as the reaction medium. The N2O5 cleaves heteroatom-silicon bonds, in silylamines and silyl ethers respectively, to yield the desired energetic groupings (nitramines or nitrate esters respectively) without liberation of acids which would occur with conventional substrates (amines or alcohols). These ...

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