118561-70-9Relevant academic research and scientific papers
2,6-Dimethyl-4-nitrobenzoic anhydride (DMNBA): An effective coupling reagent for the synthesis of carboxylic esters and lactones
Shiina, Isamu,Miyao, Ryo
experimental part, p. 1313 - 1328 (2009/07/05)
Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.
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).
Process for the production of nitro derivatives of aromatic compounds
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, (2008/06/13)
Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.
