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Patil VV, Shankarling GS. Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines. J Org Chem. 2015;80(16):7876-83doi: 10.1021/acs.joc.5b00582.
Patil, V. V., & Shankarling, G. S. (2015). Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines. The Journal of organic chemistry, 80(16), 7876-83. https://doi.org/10.1021/acs.joc.5b00582
Patil, Vilas Venunath, and Shankarling, Ganapati Subray. "Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines." The Journal of organic chemistry vol. 80,16 (2015): 7876-83. doi: https://doi.org/10.1021/acs.joc.5b00582
Patil VV, Shankarling GS. Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines. J Org Chem. 2015 Aug 21;80(16):7876-83. doi: 10.1021/acs.joc.5b00582. Epub 2015 Aug 03. PMID: 26212905.
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J Org Chem. 2015 Aug 21;80(16):7876-83. doi: 10.1021/acs.joc.5b00582. Epub 2015 Aug 03.

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

The Journal of organic chemistry

Vilas Venunath Patil, Ganapati Subray Shankarling

Affiliations

  1. Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai 400019, India.

PMID: 26212905 DOI: 10.1021/acs.joc.5b00582

Abstract

Unusual regio- and chemoselective oxidation of aromatic amines hindered with ortho substituents (except -NH2, -NHCH3, and -OH) to the corresponding nitro compounds is described by use of nonanebis(peroxoic acid). The mechanistic investigation for selective oxidation of amines ortho-substituted with -NH2 or -OH showed the involvement of H-bonding between the ortho hydrogen of the adjacent -XH group (where X = NH, NR, or O) and an oxygen atom from the diperoxy acid. Various mono- and diamines are oxidized into corresponding mononitro derivatives in high yield and purity without employing any protection strategies. The protocol was also found to successful on the gram scale.

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