Tetrahedron letters

Reactions of acyl nitroso compounds with amines: Production of nitroxyl (HNO) with the preparation of amides

RN Atkinson, BM Storey, SB King

Index: Atkinson, Robert N.; Storey, Bernadette M.; King, S. Bruce Tetrahedron Letters, 1996 , vol. 37, # 52 p. 9287 - 9290

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Citation Number: 36

Abstract

Oxidation of hydroxamic acids in the presence of amines generates nitrous oxide (N2O) and the corresponding amide. The identification of N2O suggests the intermediacy of nitroxyl (HNO). Retro-Diels Alder dissociation of cyclopentadiene-acyl nitroso compound cycloadducts releases N2O with amide formation.

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