2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines

Achim Porzelle; Anthony W. J. Cooper; Michael D Woodrow; Nicholas C.O. Tomkinson

doi:10.1055/s-0030-1258546

2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines

Achim Porzelle, Anthony W. J. Cooper, Michael D Woodrow, Nicholas C.O. Tomkinson

Pure And Applied Chemistry

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Abstract

Reaction of substituted N-aryl hydroxylamines with methanesulfonyl chloride, p-toluenesulfonyl chloride, or trifluoromethanesulfonic anhydride under basic conditions leads to the rearranged 2-aminophenols (45-94%). The overall reaction sequence can be performed using polymer-supported sulfonyl chloride resin allowing for the effective conversion of N-aryl hydroxylamines to the 2-aminophenols without the need for chromatography.

Original language	English
Pages (from-to)	2471-2473
Number of pages	3
Journal	Synlett
Volume	2010
Issue number	16
DOIs	https://doi.org/10.1055/s-0030-1258546
Publication status	Published - Oct 2010

Keywords

rearrangement
hydroxylamine
solid-phase synthesis
2-aminophenol

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title = "2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines",

abstract = "Reaction of substituted N-aryl hydroxylamines with methanesulfonyl chloride, p-toluenesulfonyl chloride, or trifluoromethanesulfonic anhydride under basic conditions leads to the rearranged 2-aminophenols (45-94%). The overall reaction sequence can be performed using polymer-supported sulfonyl chloride resin allowing for the effective conversion of N-aryl hydroxylamines to the 2-aminophenols without the need for chromatography.",

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author = "Achim Porzelle and Cooper, {Anthony W. J.} and Woodrow, {Michael D} and Tomkinson, {Nicholas C.O.}",

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AU - Porzelle, Achim

AU - Cooper, Anthony W. J.

AU - Woodrow, Michael D

AU - Tomkinson, Nicholas C.O.

PY - 2010/10

Y1 - 2010/10

N2 - Reaction of substituted N-aryl hydroxylamines with methanesulfonyl chloride, p-toluenesulfonyl chloride, or trifluoromethanesulfonic anhydride under basic conditions leads to the rearranged 2-aminophenols (45-94%). The overall reaction sequence can be performed using polymer-supported sulfonyl chloride resin allowing for the effective conversion of N-aryl hydroxylamines to the 2-aminophenols without the need for chromatography.

AB - Reaction of substituted N-aryl hydroxylamines with methanesulfonyl chloride, p-toluenesulfonyl chloride, or trifluoromethanesulfonic anhydride under basic conditions leads to the rearranged 2-aminophenols (45-94%). The overall reaction sequence can be performed using polymer-supported sulfonyl chloride resin allowing for the effective conversion of N-aryl hydroxylamines to the 2-aminophenols without the need for chromatography.

KW - rearrangement

KW - hydroxylamine

KW - solid-phase synthesis

KW - 2-aminophenol

U2 - 10.1055/s-0030-1258546

DO - 10.1055/s-0030-1258546

M3 - Article

SN - 0936-5214

VL - 2010

SP - 2471

EP - 2473

JO - Synlett

JF - Synlett

IS - 16

ER -

2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines

Abstract

Keywords

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