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 (https://doi.org/10.1055/s-0030-1258546)

[thumbnail of 2_aminophenols.pdf]
Preview
PDF. Filename: 2_aminophenols.pdf
Final Published Version

Download (76kB)| Preview

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.