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

Stephen G. Davies; John F. Fox; Simon Jones; Anne J. Price; Miguel A. Sanz; Thomas G.R. Sellers; Andrew D. Smith; FÁtima C. Teixeira

doi:10.1039/b205323n

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

Stephen G. Davies^*, John F. Fox, Simon Jones, Anne J. Price, Miguel A. Sanz, Thomas G.R. Sellers, Andrew D. Smith, FÁtima C. Teixeira

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

He 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.

Original language	English
Pages (from-to)	1757-1765
Number of pages	9
Journal	Journal of the Chemical Society. Perkin Transactions 1
Volume	2
Issue number	15
DOIs	https://doi.org/10.1039/b205323n
Publication status	Published - 31 May 2002

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

abstract = "He 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.",

author = "Davies, {Stephen G.} and Fox, {John F.} and Simon Jones and Price, {Anne J.} and Sanz, {Miguel A.} and Sellers, {Thomas G.R.} and Smith, {Andrew D.} and Teixeira, {F{\'A}tima C.}",

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T1 - The [2,3] sigmatropic rearrangement of N-benzyl-O-allylhydroxylamines

AU - Davies, Stephen G.

AU - Fox, John F.

AU - Jones, Simon

AU - Price, Anne J.

AU - Sanz, Miguel A.

AU - Sellers, Thomas G.R.

AU - Smith, Andrew D.

AU - Teixeira, FÁtima C.

PY - 2002/5/31

Y1 - 2002/5/31

N2 - He 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.

AB - He 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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U2 - 10.1039/b205323n

DO - 10.1039/b205323n

M3 - Article

AN - SCOPUS:0035995701

SN - 1472-7781

VL - 2

SP - 1757

EP - 1765

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 15

ER -

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

Abstract

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