Electrophilic Aromatic Nitration Using a Mixed Catalyst of Lithium, Molybdenum, Ytterbium on Silica Gel

Advanced Synthesis and Catalysis

Volumn 345, Issue 12, 2003, Pages 1329-1333

  Shi, Min ^a   Cui, Shi Cong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Catalyst recycling; Halogenated solvent free aromatic nitration; Lithium; Mixed catalyst; Molybdenum; Perfluorinated rare earth metal salt; Silica gel; Ytterbium

Indexed keywords

CHLORINE DERIVATIVE; LITHIUM DERIVATIVE; MOLYBDENUM; NITRIC ACID; OXYGEN; PERFLUOROOCTANE; SILICA GEL; SOLVENT; SULFONE DERIVATIVE; YTTERBIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; NITRATION;

EID: 1642432914     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303129     Document Type: Article

References (24)

1. nd ed., Cornell University Press, Ithaca, New York, 1969.
2. G. A. Olah, S. J. Kuhn, in Friedel-Crafts and Related Reactions, (Ed.: G. A. Olah), Wiley-Interscience, New York, Vol. 2, 1964.
3. G. A. Olah, ACS Symposium Series, Vol. 22, (Ed.: F. Albright), American Chemical Society, Washington DC, 1967, p. 1.
4. J. G. Hoggett, R. B. Moodie, J. R. Penton, K. Schofield, Nitration and Aromatic Reactivity, Cambridge University Press, London, 1971.
5. K. Schofield, Aromatic Nitration, Cambridge University Press, London, 1980.
6. G. A. Olah, R. Malhotra, S. C. Narang, Nitration: Methods and Mechanism, (Ed.: H. Feuer), VCH Publishers, New York, 1989.
7. L. V. Malysheva, E. A. Paukshtis, K. G. Ione, Catal. Rev. Sci. Eng. 1995, 37, 179-226.
8. a) F. J. Waller, A. G. M. Barrett, D. C. Braddock, D. Ramprasad, Chem. Commun. 1997, 613-614;
9. b) A. G. M. Barrett, D. C. Braddock, R. Ducray, R. M. McKinnell, F. I. Waller, Synlett 2001, 57-60;
10. c) F. J. Waller, A. G. M. Barrett, D. C. Braddock, R. M. McKinnell, D. Ramprasad, J. Chem. Soc. Perkin Trans. 1 1999, 867-871;
11. d) F. I. Waller, A. G. M. Barrett, D. C. Braddock, R. M. McKinnell, A. J. P. White, D. J. Williams R. Ducray, J. Org. Chem. 1999, 64, 2910-2913.
12. a) M. Shi, S. C. Cui, J. Fluorine Chem. 2002, 113, 207-209;
13. b)M. Shi, S. C. Cui, Chem. Commun. 2002, 994-995.
14. For a survey of the Kyodai nitration, see: a) M. Matsunaga, Chimica Oggi 1994, 12, 58-61; b) T. Mori, H. Suzuki, Synlett 1995, 383-392; c) T. Suzuki, R. Noyori. Chemtracts 1997, 10, 813-817; d) J. H. Ridd, Acta Chem. Scand. 1998, 52, 11-22; e) N. Nonoyama, T. Mori, H. Suzuki, Zh. Org. Khim. 1998, 34, 1591-1594.
15. For a survey of the Kyodai nitration, see: a) M. Matsunaga, Chimica Oggi 1994, 12, 58-61; b) T. Mori, H. Suzuki, Synlett 1995, 383-392; c) T. Suzuki, R. Noyori. Chemtracts 1997, 10, 813-817; d) J. H. Ridd, Acta Chem. Scand. 1998, 52, 11-22; e) N. Nonoyama, T. Mori, H. Suzuki, Zh. Org. Khim. 1998, 34, 1591-1594.
16. For a survey of the Kyodai nitration, see: a) M. Matsunaga, Chimica Oggi 1994, 12, 58-61; b) T. Mori, H. Suzuki, Synlett 1995, 383-392; c) T. Suzuki, R. Noyori. Chemtracts 1997, 10, 813-817; d) J. H. Ridd, Acta Chem. Scand. 1998, 52, 11-22; e) N. Nonoyama, T. Mori, H. Suzuki, Zh. Org. Khim. 1998, 34, 1591-1594.
17. For a survey of the Kyodai nitration, see: a) M. Matsunaga, Chimica Oggi 1994, 12, 58-61; b) T. Mori, H. Suzuki, Synlett 1995, 383-392; c) T. Suzuki, R. Noyori. Chemtracts 1997, 10, 813-817; d) J. H. Ridd, Acta Chem. Scand. 1998, 52, 11-22; e) N. Nonoyama, T. Mori, H. Suzuki, Zh. Org. Khim. 1998, 34, 1591-1594.
18. For a survey of the Kyodai nitration, see: a) M. Matsunaga, Chimica Oggi 1994, 12, 58-61; b) T. Mori, H. Suzuki, Synlett 1995, 383-392; c) T. Suzuki, R. Noyori. Chemtracts 1997, 10, 813-817; d) J. H. Ridd, Acta Chem. Scand. 1998, 52, 11-22; e) N. Nonoyama, T. Mori, H. Suzuki, Zh. Org. Khim. 1998, 34, 1591-1594.
19. T. Miłczak, J. Jacniacki, J. Zawadzki, M. Malesa, W. Skupinski, Synth. Commun. 2001, 31, 173-187.
20. a) A. Cornelis, L.Delaude, A. Gertmans, P. Laszlo, Tetrahedron Lett. 1988, 29, 5657-5660;
21. b) P. Laszlo, J. Vandormael, Chem. Lett. 1988, 11, 1843-1846;
22. c) P. Laszlo, A. Cornelis, A. Germans, Chem. Lett. 1988, 11, 1839-1842.
23. S. Kobayashi, A. Kawada, S. Mitamura, J. Matsuo, T. Tsuchiya, Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333.
24. 3H (50% v/v) and the mixture heated at boiling for 30 min to 1 h. The mixture was filtered to remove the unreacted oxide. The water was then removed from the filtrate under reduced pressure. The resulting hydrate was dried by heating under vacuum at 180 to 200°C for 48 h.