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

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

The Journal of organic chemistry (2015-07-28)
Vilas Venunath Patil, Ganapati Subray Shankarling
摘要

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.