Side-Chain Nitration of Styrene and Para-Substituted Derivatives with a Combination of Nitrogen Dioxide and Ozone

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6498-6502

  Suzuki, Hitomi ^a   Mori, Tadashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000111730     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9705024     Document Type: Article

References (58)

1. (1)(a) Perekalin, V. V.; Lipina, E. S.; Berestovitskaya, V. M.; Efremov, D. A. Nitroalkenes, Conjugated Nitro Compounds; John Wiley & Sons, Ltd.: Chichester, 1994; Chapter 2, pp 53-168.
2. (b) Ono, N. In Organic Nitro Chemistry Series, Nitro Compounds, Recent Advances in Synthesis and Chemistry; Feuer, H., Nielsen, A. T., Eds.; VCH Publishers, Inc.: New York, 1990; Chapter 1 (pp 1-135.
3. (c) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
4. (d) Kabalka, G. W.; Guindi, L. H. M.; Varma, R. S. Tetrahedron 1990, 46, 7443.
5. (e) Kabalka, G. W.; Varma, R. S. Org. Prep. Proc. Int. 1987, 19, 283.
6. Grebenyuk, A. D.; Ismailova, R. A.; Tokbolatov, R. B.; Ovodova, T. Zh. Org. Khim. 1990, 26, 680.
7. Tinsley, S. W. J. Org. Chem. 1961, 26, 4723.
8. Sy, W.-W.; By, A. W. Tetrahedron Lett. 1985, 26, 1193.
9. (a) Masnovi, J. M.; Kochi, J. K. Recl. Trav. Chim. Pays-Bos 1986, 105, 286.
10. (b) Penczek, S.; Jagur-Grodzinski, J.; Szwarc, M. J. Am. Chem. Soc. 1968, 90, 2174.
11. (c) Schmidt, E.; Fischer, H. Chem. Ber. 1920, 53, 1529.
12. Mathew, L.; Varghese, B.; Sankararaman, S. J. Chem. Soc., Perkin Trans. 2 1993, 2399.
13. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
14. (a) Hwu, J. R.; Chen, K.-L.; Ananthan, S.; Patel, H. V. Organometallics 1996, 15, 499.
15. (b) Hwu, J. R.; Chen, K.-L.; Ananthan, S. J. Chem. Soc., Chem. Commun. 1994, 1425.
16. Hayama, T.; Tomoda, S.; Takeuchi, Y.; Nomura, Y. Tetrahedron Lett. 1982, 23, 4733.
17. Jew, S.-S.; Kim, H.-D.; Cho, Y.-S.; Cook, C.-H. Chem. Lett. 1986, 1747.
18. (a) Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3629.
19. (b) Mukaiyama, T.; Hata, E.; Yamada, T. Chem. Lett. 1995, 505.
20. For aromatic nitration using nitrogen dioxide and ozone, see: (a) Mori, T.; Suzuki, H. Synlett 1995, 383. (b) Mori, T. Ph.D. Thesis, Kyoto University, 1997; electronic version of this thesis is available via World Wide Web: URL, http://kuchem.kyoto-u.ac.jp/www/yugo/ user/tmori/th/cont.html. (c) Also, see: Suzuki, H.; Nonoyama, N. J. Chem. Soc., Chem. Commun. 1996, 1783.
21. For aromatic nitration using nitrogen dioxide and ozone, see: (a) Mori, T.; Suzuki, H. Synlett 1995, 383. (b) Mori, T. Ph.D. Thesis, Kyoto University, 1997; electronic version of this thesis is available via World Wide Web: URL, http://kuchem.kyoto-u.ac.jp/www/yugo/ user/tmori/th/cont.html. (c) Also, see: Suzuki, H.; Nonoyama, N. J. Chem. Soc., Chem. Commun. 1996, 1783.
22. For aromatic nitration using nitrogen dioxide and ozone, see: (a) Mori, T.; Suzuki, H. Synlett 1995, 383. (b) Mori, T. Ph.D. Thesis, Kyoto University, 1997; electronic version of this thesis is available via World Wide Web: URL, http://kuchem.kyoto-u.ac.jp/www/yugo/ user/tmori/th/cont.html. (c) Also, see: Suzuki, H.; Nonoyama, N. J. Chem. Soc., Chem. Commun. 1996, 1783.
23. (a) Shechter, H. Rec. Chem. Prog. 1964, 25, 55.
24. (b) Brand, J. C. D.; Stevens, I. D. R. J. Chem. Soc. 1958, 629.
25. (c) Baldock, H.; Levy, N.; Scaife, C. W. J. Chem. Soc. 1949, 2627.
26. (d) Levy, N.; Scaife, C. W.; Smith, A. E. W. J. Chem. Soc. 1948, 52.
27. (e) J. Chem. Soc. 1946, 1096.
28. (f) Levy, N.; Scaife, C. W. J. Chem. Soc. 1946, 1093.
29. (g) Seifert, W. K. J. Org. Chem. 1963, 28, 125.
30. Bryant, D. K.; Challis, B. C.; Iley, J. J. Chem. Soc., Chem. Commun. 1989, 1027.
31. Metzger, H.; Meier, H. In Methoden der Organischen Chemie, Band X/1; Stroh, H., Ed.; Georg Thieme Verlag: Stuttgart, 1971, p 891.
32. Golding, P.; Powell, J. L.; Ridd, J. H. J. Chem. Soc., Perkin Trans. 2 1996, 813.
33. (a) Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319.
34. (b) Res. Chem. Intermed. 1996, 22, 209.
35. (c) Hubig, S. M.; Bookman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 3842.
36. Giamalva, D. H.; Kenion, G. B.; Church, D. F.; Pryor, W. A. J. Am. Chem. Soc. 1987, 109, 7059.
37. Chatterjee, J.; Coombes, R. G.; Barnes, J. R.; Fildes, M. J. J. Chem. Soc., Perkin Trans. 2 1995, 1031.
38. (a) Powell, J. L.; Ridd, J. H.; Sandall, J. P. B. J. Chem. Soc., Chem. Commun. 1990, 402.
39. (b) Appl. Magn. Reson. 1993, 5, 151.
40. (a) Duynstee, E. F. J.; Housmans, J. G. H. M.; Voskuil, W.; Berix, J. W. M. Recl. Trav. Chim. Pays-Bas 1973, 92, 698.
41. (b) Michael, A.; Carlson, G. H. J. Org. Chem. 1940, 5, 14.
42. (c) Schoenbrunn, E. F.; Gardner, J. H. J. Am. Chem. Soc. 1960, 82, 4905.
43. Lewis, R. J.; Moodie, R. B. J. Chem. Soc., Perkin Trans. 2 1996, 1315.
44. 26
45. (a) Stevens, T. E.; Emmons, W. D. J. Am. Chem. Soc. 1957, 79, 6008.
46. (b) Stevens, T. E. J. Org. Chem. 1959, 24, 1136.
47. Bloom, A. J.; Fleischmann, M.; Mellor, J. M. Electrochim. Acta 1987, 32, 785.
48. Bordwell, F. G.; Garbisch, E. W., Jr. J. Org. Chem. 1962, 27, 2322.
49. For calculation methods, see: (a) Stewart, J. J. J. omput. Chem. 1989, 10, 209. (b) 1989, 10, 221. (c) Dewar, M. J. S.; Zoebish, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
50. For calculation methods, see: (a) Stewart, J. J. J. omput. Chem. 1989, 10, 209. (b) 1989, 10, 221. (c) Dewar, M. J. S.; Zoebish, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
51. For calculation methods, see: (a) Stewart, J. J. J. omput. Chem. 1989, 10, 209. (b) 1989, 10, 221. (c) Dewar, M. J. S.; Zoebish, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
52. For frontier electron densities in radical reactions, see: (a) Fukui, K.; Yonezawa, T.; Nagata, V.; Shingu, H. J. Chem. Phys. 1954, 22, 1433. (b) Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722.
53. For frontier electron densities in radical reactions, see: (a) Fukui, K.; Yonezawa, T.; Nagata, V.; Shingu, H. J. Chem. Phys. 1954, 22, 1433. (b) Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722.
54. (a) Shaik, S. S.; Pross, A. J. Am. Chem. Soc. 1989, 111, 4306.
55. (b) Shaik, S. S.; Canadell, E. J. J. Am. Chem. Soc. 1990, 112, 1452.
56. (c) Shaik, S. S. J. Org. Chem. 1990, 55, 3434.
57. (d) Pross, A. J. Am. Chem. Soc. 1986, 108, 3537.
58. (e) Pross, A.; Shaik, S. S. Acc. Chem. Res. 1983, 16, 363.