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

Autor:	Vilas V. Patil, Ganapati S. Shankarling
Rok vydání:	2015
Předmět:	Steric effects Oxygen atom Chemistry Yield (chemistry) Ortho hydrogen Organic Chemistry Nitro Organic chemistry Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 80:7876-7883
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.5b00582
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0d5ff1afd7cb5096d1e20303eb09cf25 https://doi.org/10.1021/acs.joc.5b00582 Zobrazit plný text záznamu