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

Porzelle, Achim and Cooper, Anthony W. J. and Woodrow, Michael D and Tomkinson, Nicholas C.O. (2010) 2-aminophenols containing electron-withdrawing groups from N-aryl hydroxylamines. Synlett, 2010 (16). pp. 2471-2473. ISSN 0936-5214

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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.