270
N. Iranpoor et al.
completion of the reaction, the resulting mixture was dissolved in acetone
(3 mL) and was presorbed on silica gel (5 g). The resulting silica gel
mixture was applied on a silica gel column and eluted with petroleum
ether/acetone (7 : 3) to afford 0.135 g (84%)of 2-nitro-chlorobenzene,
mp 318C [Lit.[33] 31–338C] and 4-nitrochlorobenzene mp 808C [Lit.[33]
81–828C] with ratio of 47 : 53, respectively.
REFERENCES
1. Schofield, K. Aromatic Nitration; Cambridge University Press, 1980.
2. Vogel’s. Textbook of Practical Organic Chemistry, 4th Ed.; Lonman: New York,
1987.
3. Germain, A. J. Chem. Soc. Chem. Commun. 1990, 1697.
4. Thompson, M. J.; Zeegers, P. J. Tetrahedron 1991, 47, 8787.
5. Santaniello, E.; Ravasi, M.; Ferraboschi, P. J. Org. Chem. 1983, 48, 739.
6. Bisarya, S. C.; Joshi, S. K.; Holkar, A. G. Synth. Commun. 1993, 23, 1125.
7. Crivello, J. V. J. Org. Chem. 1981, 46, 3056.
8. Poirier, J. M.; Vottero, C. Tetrahedron 1989, 45, 1415.
9. McCullough, T. J. Chem. Ed. 1990, 67, 801.
10. Thompson, M. J.; Zeegers, P. J. Tetrahedron Lett. 1988, 29, 2471.
11. Zeegers, P. J. J. Chem. Ed. 1993, 70, 1036.
12. Ouertani, G.; Girard, P.; Kagan, H. B. Tetrahedron Lett. 1982, 23, 4315.
13. Olah, G. A.; Narang, S. C.; Olah, J. A.; Lammertsma, K. Proc. Natl. Acad. Sci.
USA 1982, 4487.
14. Alazard, J. P.; Kagan, H. B.; Seeton, R. Bull. Soc. Chem. Fr. 1977, 499.
15. Cornelis, A.; Laszlo, P. Synthesis 1985, 909.
16. Cornelis, A.; Laszlo, P. Synlett 1994, 155.
17. Knowles, J. R.; Norman, R. O.C. J. Chem. Soc. 1961, 3888.
18. Kurz, M. E.; Yang, L. T.A.; Zahora, E. P.; Adams, R. C. J. Org. Chem. 1973, 38,
2271.
19. Nagy, S. M.; Yarovoy, K. A.; Shakirov, M. M.; Shubin, V. G.; Votrikova, L. A.;
Ione, K. G. J. Mol. Catal. 1991, 64, 31.
20. Masci, B. Tetrahedron 1989, 45, 2719.
21. Topia, R.; Torres, G.; Valderrama, J. A. Synth. Commun. 1986, 16, 681.
22. Pervez, H.; Onyisiuka, S. O.; Rees, L.; Rooney, J. R.; Sukling, C. J. Tetrahedron
1988, 44, 4555.
23. Samajdar, S.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 8017.
24. Fisher, A.; Mathivanan, N. Tetrahedron Lett. 1988, 29, 1869.
25. Peng, X.; Fukui; Mizutu, M.; Suzuki, H. Org. Biomol. Chem. 2003, 1, 2326.
26. Addison, C. C.; Lewis, J. J. Chem. Soc. 1951, 2843.
27. Addison, C. C. Chem. Rev. 1980, 21, 80.
28. Iranpoor, N.; Firouzabadi, H.; Zolfigol, M. A. Synth. Commun. 1998a, 28, 367.
29. Iranpoor, N.; Firouzabadi, H.; Zolfigol, M. A. Synth. Commun. 1998b, 28, 377.
30. Iranpoor, N.; Firouzabadi, H.; Zolfigol, M. A. Synth. Commun. 1997, 27, 3301.
31. Iranpoor, N.; Firouzabadi, H.; Zolfigol, M. A. Synth. Commun. 1998c, 28, 2773.
32. Mallakpour, S. E.J. Chem. Ed. 1992, 69, 238.
33. Fluka. Chemica-Biochemical; 1993/94.