
%0 Journal Article
%A Hartshorn, MP 
%A Readman, JM 
%A Robinson, WT 
%A Sies, CW 
%A Wright, GJ 
%T 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 <I>ipso</I>-Substitution
%J Australian Journal of Chemistry
%D 1988/03/01
%V 41
%N 3
%P 373-386
%K 
%R https://doi.org/10.1071/CH9880373
%U https://www.publish.csiro.au/paper/CH9880373 
%X 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). 
