
TY  - JOUR
A1  - Hartshorn, MP 
A1  - Readman, JM 
A1  - Robinson, WT 
A1  - Sies, CW 
A1  - Wright, GJ 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1988
VL  - 41
IS  - 3
SP  - 373
EP  - 386
KW  - 
UR  - https://doi.org/10.1071/CH9880373 
N2  - 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). 
ER  -

