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

…, S Jones, AJ Price, MA Sanz, TGR Sellers…

Index: Davies, Stephen G.; Fox, John F.; Jones, Simon; Price, Anne J.; Sanz, Miguel A.; Sellers, Thomas G. R.; Smith, Andrew D.; Teixeira, Fatima C. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 15 p. 1757 - 1765

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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.

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