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Issue 15, 2002
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The [2,3] sigmatropic rearrangement of N-benzyl-O-allylhydroxylamines

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Abstract

The rearrangement of a range of N-benzyl-O-allylhydroxylamines to the corresponding N-allylhydroxylamines upon treatment with n-BuLi in THF, followed by reduction to the corresponding N-allylamines, is described. Mechanistic studies of the transformation are consistent with an intramolecular [2,3] sigmatropic rearrangement.

Graphical abstract: The [2,3] sigmatropic rearrangement of N-benzyl-O-allylhydroxylamines

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Article information


Submitted
31 May 2002
Accepted
19 Jun 2002
First published
12 Jul 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1757-1765
Article type
Paper

The [2,3] sigmatropic rearrangement of N-benzyl-O-allylhydroxylamines

S. G. Davies, J. F. Fox, S. Jones, A. J. Price, M. A. Sanz, T. G. R. Sellers, A. D. Smith and F. C. Teixeira, J. Chem. Soc., Perkin Trans. 1, 2002, 1757
DOI: 10.1039/B205323N

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