Trichloroisocyanuric Acid/NaNO2/wet SiO2 as an Efficient System for the Selective Dinitration of Phenols under Solvent-free Conditions

Synlett

Volumn , Issue 14, 2003, Pages 2222-2224

  Zolfigol, Mohammad Ali ^a   Madrakian, Elaheh ^a   Ghaemi, Ezat ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

Author keywords

Dinitrophenols; Solvent free; Trichloroisocyanuric acid

Indexed keywords

CYANURIC ACID; ISOCYANIC ACID DERIVATIVE; PHENOL DERIVATIVE; SILICON DERIVATIVE; SODIUM NITRITE; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; NITRATION; ROOM TEMPERATURE;

EID: 0242575792     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42063     Document Type: Article

References (32)

1. Esakkidurai, T.; Pitchumani, K. J. Mol. Catal A: Chem. 2002, 185, 305.
2. Iranpoor, N.; Firouzabadi, H.; Heydari, R. Synth. Commun. 1999, 29, 3295.
3. Zolfigol, M. A.; Ghaemi, E.; Madrakian, E. Synlett 2003, 191; and references cited therein.
4. Rajagopal, R.; Srinivasan, K. V. Ultrason. Sonochem. 2003, 10, 41.
5. Iranpoor, N.; Firouzabadi, H.; Heydari, R. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1027.
6. Crivello, J. V. J. Org. Chem. 1981, 46, 3056.
7. Poirier, J. M.; Vottero, C. Tetrahedron 1989, 45, 1415.
8. Laszlo, P. Acc. Chem. Res. 1986, 19, 121.
9. Laszlo, P.; Cornelis, A. Synlett 1994, 155.
10. (a) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
11. (b) Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61.
12. (c) Varma, R. S. Green Chem. 1999, 1, 43.
13. (a) Zolfigol, M. A. Tetrahedron 2001, 57, 9509; also see our references cited therein.
14. (b) Zolfigol, M. A.; Torabi, M.; Mallakpour, S. E. Tetrahedron 2001, 57, 8381.
15. (c) Zolfigol, M. A.; Bamoniri, A. Synlett 2002, 1621.
16. (d) Zolfigol, M. A.; Shirini, F.; Ghorbani-Choghamarani, A.; Mohammadpoor-Baltork, I. Green Chem. 2002, 4, 562.
17. (a) Zolfigol, M. A.; Ghorbani-Choghamarani, A.; Hazarkhani, H. Synlett 2002, 1002.
18. (b) Zolfigol, M. A.; Madrakian, E.; Ghaemi, E.; Mallakpour, S. E. Synlett 2002, 1633.
19. (a) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Synlett 2001, 1641.
20. (b) Xiog, Z. X.; Huang, N. P.; Zhong, P. Synth. Commun. 2001, 31, 245.
21. (c) Mendonca, G. F.; Sanseverino, A. M.; Mattos, M. C. S. D. Synthesis 2003, 41.
22. (d) Mendonca, G. F.; Sanseverino, A. M.; de Mattos, M. C. S. Synlett 2003, 45.
23. (a) Maleski, R. J. Synth. Commun. 1993, 23, 343.
24. (b) Maleski, R. J. Synth. Commun. 1995, 25, 2327.
25. (c) Ross, D. S.; Hum, G. P.; Blucher, W. G. J. Chem. Soc., Chem. Commun. 1980, 532.
26. (d) Al-Obaidi, V.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1985, 467.
27. Suboch, G. A.; Belyaev, E. Y. Russ. J. Org. Chem. 1998, 34, 288.
28. (a) Ishikawa, T.; Watanabe, T.; Tanigawa, H.; Saito, T.; Kotake, K. I.; Ohashi, Y.; Ishii, H. J. Org. Chem. 1996, 61, 2774.
29. (b) Beake, B. D.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1998, 1; and references cited therein.
30. Zolfigol, M. A.; Bagherzadeh, M.; Madrakian, E.; Ghaemi, E.; Taqian-nasab, A. J. Chem. Res, Synop. 2001, 140.
31. Dichloromethane is the best solvent for the extraction of dinitrophenols due to its low boiling point. We know that dinitrophenols are very volatile (due to intramolecular hydrogen bonding) and should them be distilled with high boiling point solvents the yield of reactions will result decreased.
32. Dictionary of Organic Compounds, 3th Ed., Vol. 2; Eyre and Spottiswoode: London, 1965, 620.