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 (free Supporting Information)
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.
see article for more examples