AROMATIC-SUBSTITUTION .44. SUPERACID-CATALYZED TRANSFER NITRATION OF BENZENE, TOLUENE, AND MESITYLENE WITH 9-NITROANTHRACENE AND PENTAMETHYLNITROBENZENE - EVIDENCE FOR THE REVERSIBILITY OF ELECTROPHILIC AROMATIC NITRATION IN SPECIFIC CASES

被引:23
作者
OLAH, GA
NARANG, SC
MALHOTRA, R
OLAH, JA
机构
[1] Hydrocarbon Research Institute, University of Southern California, University Park, Los Angeles
关键词
D O I
10.1021/ja00501a028
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reversibility of electrophilic aromatic nitration was proven in certain, specific cases of superacid-catalyzed transfer nitration reactions. In the reaction of benzene, toluene, and mesitylene with 9-nitroanthracene and pentamethylnitrobenzene, nitrobenzene, nitrotoluenes, and nitromesitylene were obtained in the presence of superacids. The primary kinetic hydrogen isotope effect, kHkD, of 2.25 ± 0.05 in the nitration of anthracene-d10 with nitronium hexafluorophosphate in nitromethane solution is also in accord with the reversibility of the nitration of anthracene. © 1979, American Chemical Society. All rights reserved.
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页码:1805 / 1807
页数:3
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