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

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

8 Citations (Scopus)

312 Downloads (Pure)

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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2 aminophenolsFinal published version, 74.9 KB

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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.",

keywords = "rearrangement, hydroxylamine, solid-phase synthesis, 2-aminophenol",

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

year = "2010",

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language = "English",

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T1 - 2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines

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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