Regioselective double Kyodai nitration of toluene and chlorobenzene over zeolites. High preference for the 2,4-dinitro isomer at the second nitration stage

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3431-3434

  Peng, Xinhua ^a   Suzuki, Hitomi ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

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ARTICLE;

EID: 0001741231     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016283x     Document Type: Article

References (17)

1. (a) Harris, G. F. P. In Industrial and Laboratory Nitrations: Albright, L. F., Hanson, C., Eds.; American Chemical Society: Washington, DC, 1975; p 313.
2. (b) Hermann, H.; Gebauer, J.; Konieczny, P. In Nitration. Recent Laboratory and Industrial Developments; Albright, L. F., Carr, R. V. C., Schmitt, R. J., Eds.; American Chemical Society: Washington, DC, 1995; p 234.
3. For a survey of the Kyodai nitration, see: (a) Mori, T.; Suzuki, H. Synlett 1995, 383-392.
4. (b) Suzuki, T.; Noyori, R. Chemtracts 1997, 10, 813-815.
5. (c) Nonoyama, N.; Mori, T.; Suzuki, H. Zh. Obshch. Khim. 1998, 34, 1591-1601.
6. (a) Smith, K.; Musson, A.; DeBoos, G. A. J. Org. Chem. 1998, 63, 8448-8454.
7. (b) Smith, K.; Gibbins, T.; Millar, R. W.; Claridge, R. P. J. Chem. Soc., Perkin Trans. 1 2000, 2753-2758.
8. (c) Smith, K.; Almeer, S.; Black, S. J. Chem. Commun. 2000, 1571-1572.
9. A typical isomer distribution of traditional dinitration product of toluene is 2,4-75%; 2,6-19%; 3,4-2,5%; 2,3-1.0%, and 2,5-0,5%. Adkins, R. L. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Wiley: New York, 1996; Vol. 17, pp 150-151.
10. Waller, F. J.; Barrett, A. G. M.; Braddock, D. C.; Ramprasad, D. Tetrahedron Lett. 1998, 39, 1641-1642.
11. Gigante, B.; Prazeres, A. O.; Marcelo-Curto, M. J.; Cornelis, A.; Laszlo, P. J. Org. Chem. 1995, 60, 3445-3447.
12. Hoffman, E. J.; Dame, P. A. J. Am. Chem. Soc. 1919, 41, 1013-1020.
13. Claridge, R. P.; Lancaster, N. L.; Millar, R. W.; Moodie, R. B.; Sandall, J. P. B. J. Chem. Soc., Perkin Trans. 2 2001, 197-200.
14. Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans. 1 1996, 677-683.
15. Suzuki, H.; Murashima, T.; Mori, T. J. Chem. Soc., Perkin Trans. 1 1991, 1591-1597.
16. On treatment with excess mixed acid, p-nitrotoluene gives almost exclusively the 2,4-dinitro isomer (>99%), while o-nitrotoluene affords a 67:33 mixture of 2.4-and 2.6-dinitro isomers. Booth, G. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Schulz, G., Eds.; VCH: New York, 1991; Vol. A17, p 421. On similar treatment, o-chloronitrobenzene yields 2,4-and 2,6-dinitro compounds in a ratio of 10.6:1. Claridge, R. P.; Lancaster, N. L.; Millar, R. W.; Moodie, R. B.; Sandall, J. P. B. J. Chem. Soc., Perkin Trans. 2 1999, 1815-1818.
17. On treatment with excess mixed acid, p-nitrotoluene gives almost exclusively the 2,4-dinitro isomer (>99%), while o-nitrotoluene affords a 67:33 mixture of 2.4-and 2.6-dinitro isomers. Booth, G. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Schulz, G., Eds.; VCH: New York, 1991; Vol. A17, p 421. On similar treatment, o-chloronitrobenzene yields 2,4-and 2,6-dinitro compounds in a ratio of 10.6:1. Claridge, R. P.; Lancaster, N. L.; Millar, R. W.; Moodie, R. B.; Sandall, J. P. B. J. Chem. Soc., Perkin Trans. 2 1999, 1815-1818.