JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Electrophilic Aromatic Nitration
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phy to afford compound 10a (147.7 mg) in 72% yield. White
form; 1H NMR (400 MHz, CDCl3) d 7.78 (d, 1H, J = 8.4 Hz), 7.61
(s, 1H), 7.50 (d, 1H, J = 8.4 Hz), 2.50 (s, 1H); 13C NMR (100
MHz, CDCl3) d 145.9 (q, 3JCF = 2.1 Hz); 144.2, 133.3, 128.4 (q,
3JCF = 5.9 Hz), 126.1, 125.1, 123.5 (q, 2JCF = 34.3 Hz), 21.2; FTIR
(film): 3122, 2931, 1599, 1539, 1413, 1360, 1319, 1277, 1209,
1177, 1142, 1051, 896.7, 796.6, 759.2, 661.8, 635.1 cm-1. Anal.
calcd for C8H6F3NO2: C, 46.84; H, 2.95; N, 6.83. Found: C,
46.98; H, 2.99; N, 6.96. For more details, see supporting informa-
tion.
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ACKNOWLEDGEMENTS
7. The deprotonation process may become the rate-determining
step in some special cases with weak electrophiles and
sterically hindered aromatic reactants as starting materials.
See: Zollinger, H. Adv. Phys. Org. Chem. 1964, 2, 163-200.
8. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334–338.
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This work was supported by the Science and Technol-
ogy Development Project of Weihai (2011DXGJ13,
2012DXGJ02), the Science and Technology Development
Project of Shandong (2013GGA10075), HIT.NSRIF
(2011097, 2011098), HITWH (201105, 201106) and the
Natural Science Foundation of Shandong (ZR2012BM002).
We deeply thank Prof. Vincent Gandon (Université Paris-
Sud 11, Orsay) for helpful calculations and discussions.
10. Olah, G. A.; Lin, H. C. J. Am. Chem. Soc. 1974, 96, 549-553.
11. (a) Liu, Y. K.; Lou, S. J.; Xu, D. Q.; Xu, Z. Y. Chem. Eur. J.
2010, 16, 13590-13593. (b) Zhang, L.; Liu, Z. H.; Li, H. Q.;
Fang, G. C.; Barry, B. D.; Belay, T. A.; Bi, Z. H.; Liu, Q. Org.
Lett. 2011, 13, 6536-6539. (c) Zhang, W.; Lou, S. J.; Liu, Y.
K.; Xu, Z. Y. J. Org. Chem. 2013, 78, 5932-5948.
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J. Chin. Chem. Soc. 2014, 61, 1307-1312
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