118561-71-0Relevant academic research and scientific papers
The Nitration of 4-Methylphenol, 3,4-Dimethylphenol and 3,4,5-Trimethylphenol with Nitrogen Dioxide
Hartshorn, Michael P.,Judd, Maurice C.,Vannoort, Richard W.,Wright, Graeme J.
, p. 689 - 697 (2007/10/02)
Reaction of 4-methylphenol (1a) with excess nitrogen dioxide in either benzene or dichloromethane gives the 4-nitro dienone (2a) and the 2,6-dinitrophenol (5).Similar reactions of 3,4-dimethylphenol (1b) yields the 4-nitro dienone (2b), the 2,6-dinitrophe
The Nitration of 3,4,5,6-Tetramethylbenzene-1,2-dicarbonitrile, 2,3,5,6-Tetramethylbenzonitrile, 1,2,3-Trimethyl-4,6-dinitrobenzene and 1,2,4,5-Tetramethyl-3,6-dinitrobenzene. Methyl Migrations Following ipso-Substitution
Hartshorn, Michael P.,Readman, Jennifer M.,Robinson, Ward T.,Sies, Christiaan W.,Wright Graeme J.
, p. 373 - 386 (2007/10/02)
Nitration of 3,4,5,6-tetramethylbenzene-1,2-dicarbonitrile (1a) gives epimeric pairs of dinitro ketones (6a) and (7a), and hydroxy ketones (9) and (10), in addition to the benzyl nitrate (4) and phthalide (5).Nitration of 2,3,5,6-tetramethylbenzonitrile (11) gives the epimeric dinitro ketones (15) and (16), in addition to the nitrobenzonitrile (12) and the nitrophthalide (13).Nitration of 1,2,3-trimethyl-4,6-dinitrobenzene (17) gives dimethylpropanedioic acid (23), the dinitrobenzoic acid (24), and the hydroxy dienone (25).Nitration of 1,2,4,5-tetramethyl-3,6-dinitrobenzene (18) gives dimethylpropanedioic acid (23), the dinitrobenzoic acid (26), and the nitro dicarboxylic acid (27).The formation of compounds (6a), (7a), (9), (10), (15), (16), (23) and (27) all involve methyl migrations following nitronium ion attack ipso to the migrating methyl group.X-Ray structure determinations are reported for compounds (6a), (9) and (15).
