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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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Publication details

The article was received on 31 May 2002, accepted on 19 Jun 2002 and first published on 12 Jul 2002


Article type: Paper
DOI: 10.1039/B205323N
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 1757-1765
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    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, 0, 1757
    DOI: 10.1039/B205323N

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