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Synthesis 1994; 1994(10): 1096-1105
DOI: 10.1055/s-1994-25645
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Anionic Hetero[3,3] and [3,5] Rearrangements of Hydroxylamine Derivatives Accompanied with N-O Bond Cleavage

Yasuyuki Endo* , Takuya Uchida, Shoji Hizatate, Koichi Shudo
  • *Faculty of Pharmaceutical Sciences, University of Tokyo, 7-3-1, Hongo, Tokyo 113, Japan
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Publication Date:
27 September 2002 (online)

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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,O- diacylhydroxylamines and N-acylhydroxylamine-O-carbamates result in C-C or C-N bond formation with cleavage of the N -O bond.