Synthesis

Anionic Hetero [3, 3] and [3, 5] Rearrangements of Hydroxylamine Derivatives Accompanied with NO Bond Cleavage

Y Endo, T Uchida, S Hizatate, K Shudo

Index: Endo; Uchida; Hizatate; Shudo Synthesis, 1994 , # 10 p. 1096 - 1105

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Citation Number: 7

Abstract

Aromatic and aliphatic N, O-divinylhydroxylamine systems generated in situ from hydroxylamine derivatives smoothly undergo [3, 3] rearrangement. The base-catalyzed formation and rearrangement of enolates or dienolates of N-aryl-O-acylhydroxylamines, N, 0- diacylhydroxylamines and N-acylhydroxylamine-0-carbamates result in C—C or C—N bond formation with cleavage of the N* O bond. The usefulness of [3, 3] sigmatropic ...