Application of the nitrosoamide reaction to hydrazones

RH McGirk, CR Cyr, WD Ellis…

Index: McGirk,R.H. et al. Journal of Organic Chemistry, 1974 , vol. 39, # 26 p. 3851 - 3855

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Citation Number: 7

Abstract

Nitrosation of the N-acetylhydrazones of benzophenone, acetophenone, cyclohexanone, and heptaldehyde af-fords the corresponding 1-acetoxy-1-azido compounds, ketones (or aldehydes), and acetyl azide as the principal products. The unstable N-nitrosoamide is undoubtedly formed in the first step of the reaction; a rearrangement to a diazo ester and migration of the carboxylate group complete the process. Minor products of the reaction ...