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

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

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.
LanguageEnglish
Pages2471-2473
Number of pages3
JournalSynlett
Volume2010
Issue number16
DOIs
Publication statusPublished - Oct 2010

Fingerprint

Hydroxylamines
Electrons
Anhydrides
Chromatography
Polymers
Resins
2-aminophenol

Keywords

  • rearrangement
  • hydroxylamine
  • solid-phase synthesis
  • 2-aminophenol

Cite this

Porzelle, Achim ; Cooper, Anthony W. J. ; Woodrow, Michael D ; Tomkinson, Nicholas C.O. / 2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines. In: Synlett. 2010 ; Vol. 2010, No. 16. pp. 2471-2473.
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2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines. / Porzelle, Achim; Cooper, Anthony W. J.; Woodrow, Michael D; Tomkinson, Nicholas C.O.

In: Synlett, Vol. 2010, No. 16, 10.2010, p. 2471-2473.

Research output: Contribution to journalArticle

TY - JOUR

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

VL - 2010

SP - 2471

EP - 2473

JO - Synlett

T2 - Synlett

JF - Synlett

SN - 0936-5214

IS - 16

ER -