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Synlett 2010(16): 2471-2473
DOI: 10.1055/s-0030-1258546
DOI: 10.1055/s-0030-1258546
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
2-Aminophenols Containing Electron-Withdrawing Groups from N-Aryl Hydroxylamines
Further Information
Received
19 July 2010
Publication Date:
26 August 2010 (online)
Publication History
Publication Date:
26 August 2010 (online)
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.
Key words
rearrangement - hydroxylamine - solid-phase synthesis - 2-aminophenol
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References and Notes
All rearrangement products were characterised by ¹H NMR, ¹³C NMR, LRMS, and HRMS.