Design of ionic liquid 3-methyl-1-sulfonic acid imidazolium nitrate as reagent for the nitration of aromatic compounds by in situ generation of NO 2 in acidic media

Journal of Organic Chemistry

Volumn 77, Issue 7, 2012, Pages 3640-3645

  Zolfigol, Mohammad A ^a   Khazaei, Ardeshir ^a   Moosavi Zare, Ahmad R ^a   Zare, Abdolkarim ^b   Kruger, Hendrik G ^c   Asgari, Zhila ^a   Khakyzadeh, Vahid ^a   Kazem Rostami, Masoud ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC IONIC LIQUIDS; ACIDIC MEDIA; ANILINE DERIVATIVES; IMIDAZOLIUM; IN-SITU; NITRATING AGENTS; NITROARENES; NITROGEN DIOXIDES;

AROMATIZATION; BROMINE COMPOUNDS; IONIC LIQUIDS; NITROGEN OXIDES;

NITRATION;

3 METHYL 1 SULFONIC ACID IMIDAZOLIUM NITRATE; ANILINE DERIVATIVE; AROMATIC COMPOUND; BRONSTED ACID; IMIDAZOLE DERIVATIVE; IONIC LIQUID; NITROGEN DIOXIDE; REAGENT; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; NITRATION; REACTION ANALYSIS;

EID: 84859599061     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300137w     Document Type: Article

References (36)

1. Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2008.
2. Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789
3. Cheng, G.; Duan, X.; Qi, X.; Lu, C. Catal. Commun. 2008, 10, 201-204
4. Hallett, J. P.; Welton., T. Chem. Rev. 2011, 111, 3508-3576
5. Pavlinac, J.; Zupan, M.; Laali, K. K.; Stavber, S. Tetrahedron 2009, 65, 5625-5662
6. Olivier-Bourbigou, H.; Magna, L.; Morvan, D. Appl. Catal., A 2010, 373, 1-56
7. Zare, A.; Moosavi-Zare, A. R.; Merajoddin, M.; Zolfigol, M. A.; Hekmat-Zadeh, T.; Hasaninejad, A.; Khazaei, A.; Mokhlesi, M.; Khakyzadeh, V.; Derakhshan-Panah, F.; Beyzavi, M. H.; Rostami, E.; Arghoon, A.; Roohandeh, R. J. Mol. Liq. 2012, 167, 69-77
8. Zolfigol, M. A.; Khazaei, A.; Moosavi-Zare, A. R.; Zare, A. Org. Prep. Proced. Int. 2010, 42, 95-102
9. Zolfigol, M. A.; Khazaei, A.; Moosavi-Zare, A. R.; Zare, A. J. Iran. Chem. Soc. 2010, 7, 646-651
10. Khazaei, A.; Zolfigol, M. A.; Moosavi-Zare, A. R.; Zare, A. Sci. Iran., Trans. C 2010, 17, 31-36
11. Zolfigol, M. A.; Khazaei, A.; Moosavi-Zare, A. R.; Zare A. Khakyzadeh, V. Appl. Catal., A. 2011, 400, 70-81
12. Khazaei, A.; Zolfigol, M. A.; Moosavi-Zare, A. R.; Zare, A.; Ghaemi, E.; Khakyzadeh, V.; Asgari, Z.; Hasaninejad, A. Sci. Iran., Trans. C 2011, 18, 1365-1371
13. Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Tetrahedron 2010, 66, 9077-9106
14. Zolfigol, M. A.; Mirjalili, B. F.; Bamoniri, A.; K. Zarchi, M. A.; Zarei, A.; Khazdooz, L.; Noei, J. Bull. Korean Chem. Soc. 2004, 25, 1414-1416
15. Zolfigol, M. A.; Madrakian, E.; Ghaemi, E. Synlett 2003, 2222-2224
16. Zolfigol, M. A.; Madrakian, E.; Ghaemi, E. Molecules 2002, 7, 734-742
17. Iranpoor, N.; Firouzabadi, H.; Heydari, R. Synth. Commun. 1999, 29, 3295-3305
18. Bosnich, B.; Nyholm, R. S.; Pauling, P. J.; Tobe, M. L. J. Am. Chem. Soc. 1968, 90, 4741-4742
19. Peng, X.; Suzuki, H.; Lu, C. Tetrahedron Lett. 2001, 42, 4357-4359
20. Hajipour, A. R.; Ruoho, A. E. Tetrahedron Lett. 2005, 46, 8307-8310
21. Chaubal, N. S.; Sawant, M. R. Catal. Commun. 2006, 7, 443-449
22. Shi, M.; Cui, S.-C. Chem. Commun. 2002, 994-995
23. Lancaster, N. L.; Llopis-Mestre, V. Chem. Commun. 2003, 2812-2813
24. Earle, M. J.; Katdare, S. P.; Seddon, K. R. Org. Lett. 2004, 6, 707-710
25. Laali, K. K.; Gettwert, V. J. J. Org. Chem. 2001, 66, 35-40
26. Cheng, G.; Duan, X.; Qi, X.; Lu, C. Catal. Commun. 2008, 10, 201-204
27. Smith, K.; Liu, S.; El-Hiti, G. A. Eng. Chem. Res. 2005, 44, 8611-8615
28. Holleman, A. F.; Wiberg, E. Inorganic Chemistry; Academic Press: San Diego, 2001.
29. Jolly, W. L. The Synthesis and Characterization of Inorganic Compounds; Prentice Hall: London, 1970.
30. Kennedy, G. A.; Hanrahan, R. J. J. Phys. Chem. 1974, 78, 366-371
31. Zhang, P.; Cedilote, M.; Cleary, T. P.; Pierce, M. E. Tetrahedron Lett. 2007, 46, 8659-8664
32. Chawla, H. M.; Mittal, R. S. Synthesis 1985, 70-72
33. Farmer, R. C. J. Chem. Soc. 1959, 3430-3433
34. Kinsley, A. D.; Plant, S. G. P. J. Chem. Soc. 1956, 4814-4817
35. Sura, T. P.; Ramana, M. M. V.; Kudav, N. A. Synth. Commun. 1988, 18, 2161-2165
36. Boyer, J. H.; Moran, T.; Pillai, T. P. J. Chem. Soc.,Chem. Commun. 1983, 1388-1389