Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines

Vilas Venunath Patil and Ganapati Subray Shankarling*

*Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai 400019, India, Email: gs.shankarlingictmumbai.edu.in

V. V. Patil, G. S. Shankarling, J. Org. Chem., 2015, 80, 7876-7883.

DOI: 10.1021/acs.joc.5b00582

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Abstract

The use of nonanebis(peroxoic acid) enables a regio- and chemoselective oxidation of aromatic amines hindered with an ortho substituent to the corresponding nitro compounds, except for anilines ortho-substituted with amino groups (NH₂, NHR) or hydroxyl groups, where H-bonding between an hydrogen of the adjacent group and an oxygen atom from the diperoxy acid directs the oxidation.

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Key Words

nitro compounds, peroxy acids

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ID: J42-Y2015