Regioselectivity nitration of aromatics with N2O5 in PEG-based dicationic ionic liquid

Tetrahedron Letters

Volumn 52, Issue 13, 2011, Pages 1452-1455

  Wang, Peng Cheng ^a   Lu, Ming ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Aromatic nitration; N2O5; PEG200 DAIL; Recyclable; Regioselective

Indexed keywords

1 TERT BUTYL 2 NITROETHYLBENZENE; 1 TERT BUTYL 3 NITROBENZENE; 1 TERT BUTYL 4 NITROBENZENE; 1,2 DINITROBENZENE; 1,3 DINITROBENZENE; 1,4 DINITROBENZENE; 2 ME 3 NITROBENZOIC ACID; 2 ME 5 NITROBENZOIC ACID; 2 NITROBROMOBENZENE; 2 NITROETHYLBENZENE; 2 NITROFLUOROBENZENE; 2,4 DINITROTOLUENE; 3 ME 2 NITROBENZOIC ACID; 3 ME 4 NITROBENZOIC ACID; 3 ME 6 NITROBENZOIC ACID; 3 NITROBENZOIC ACID; 3 NITROBROMOBENZENE; 3 NITROETHYLBENZENE; 3 NITROFLUOROBENZENE; 3,5 DINITRO 2 TOLUIC ACID; 4 BROMONITROBENZENE; 4 NITROETHYLBENZENE; 4 NITROFLUOROBENZENE; AROMATIC COMPOUND; BENZENE; CARBON TETRACHLORIDE; DICATIONIC ACIDIC IONIC LIQUID; IONIC LIQUID; MACROGOL 200; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NITRATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 79951955544     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.053     Document Type: Article

References (26)

1. G.A. Olah, R. Malhotra, and S.C. Narang Nitration, Methods and Mechanisms 1989 VCH New York
2. K. Schofield Aromatic Nitration 1980 Cambridge University Press Cambridge
3. R. Taylor Electrophilic Aromatic Substitution 1990 John Wiley and Sons Chichester
4. A. Cornelis, L. Delaude, A. Gerstmanns, and P. Laszlo Tetrahedron Lett. 29 1988 5909
5. B.M. Choudary, M. Ravichandra Sarma, and K. Vijaya Kumar J. Mol. Catal. 87 1994 33
6. R.P. Claridge, N.L. Lancaster, R.W. Millar, R.B. Moodie, and J.P.B. Sandall J. Chem. Soc., Perkin Trans. 2 2001 197
7. R.P. Claridge, N.L. Lancaster, R.W. Millar, R.B. Moodie, and J.P.B. Sandall J. Chem. Soc., Perkin Trans. 2 1999 1815
8. K. Smith, S. Almeer, and C. Peters Chem. Commun. 2001 2748
9. D. Vassena, A. Kogelbauer, and R. Prins Catal. Today 60 2000 275
10. M. Haouas, S. Bernasconi, A. Kogelbauer, and R. Prins Phys. Chem. Chem. Phys. 3 2001 5067
11. M.R. Crampton, L.M. Gibbons, and R. Millar J. Chem. Soc., Perkin Trans. 2 2001 1662
12. M.R. Crampton, E.L. Cropper, L.M. Gibbons, and R.W. Millar Green Chem. 4 2002 275
13. K.K. Laali, and V.J. Gettwert J. Org. Chem. 66 2001 35
14. K. Smith, S. Liu, and G.A. El-Hiti Ind. Eng. Chem. Res. 44 2005 8611
15. K. Qiao, H. Hagiwara, and C. Yokoyama J. Mol. Catal. A: Chem. 246 2006 65
16. K. Qiao, and C. Yokoyama Chem. Lett. 33 2004 808
17. R. Rajagopal, and K.V. Srinivasan Ultrason. Sonochem. 101 2003 41
18. D. Fang, Q.R. Shi, and J. Cheng Appl. Catal., A 345 2008 158
19. R.W. Millar, and S.P. Philbin Tetrahedron 53 1997 4371
20. M.B. Talawar, R. Sivabalan, B.G. Polke, U.R. Nair, G.M. Gore, and S.N. Asthana J. Hazard. Mater. 124 2005 153
21. H. Qian, Z.W. Ye, and C.X. Lv Ultrason. Sonochem. 15 2008 326
22. H.Z. Zhi, C. Lv, Q. Zhang, and J. Luo Chem. Commun. 2009 2878
23. H.Z. Zhi, J. Luo, G.A. Feng, and C.X. Lv Chin. Chem. Lett. 20 2009 379
24. 4 (15 ml), 50 °C, 2 h.
25. 4 (15 ml), 50 °C, 2 h.
26. 5 was added with stirring. After adding, temperature was raised to 50 °C and kept for 2 h. The final solution was cooled to room temperature and separated. Then the organic phase was washed once with 10%M sodium bicarbonate solution (50 ml) and twice with distilled water (50 ml). After dried over magnesium sulfate, the solvent was evaporated to spontaneously crystallize after several hours. The constituents were confirmed based on GC or LC analysis (comparison with an authentic sample).