Preference of the mesolytic cleavage over the nuclear substitution observed in the ozone-mediated nitration of bicumene with nitrogen dioxide. Implication to the electron transfer nature of the Kyodai-nitration of arenes

Chemistry Letters

Volumn , Issue 8, 1996, Pages 647-648

  Suzuki, Hitomi ^a   Mori, Tadashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030502448     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.647     Document Type: Article

References (21)

1. For a survey, see: T. Mori and H. Suzuki, Synlett, 1995, 383.
2. a) H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1996, 677; 1994, 479;
3. a) H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1996, 677; 1994, 479;
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5. a) L. Bardi, E. Fasani, and A. Albini, J. Chem. Soc., Perkin Trans. 1, 1994, 545;
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8. d) E. Baciocchi and R. Ruzziconi, J. Chem. Soc. Chem. Commun., 1984, 445;
9. e) D. M. Camaioni, and J. A. Franz, J. Org. Chem., 49, 1607 (1984);
10. f) L. W. Reichel, G. W. Griffin, A. J. Muller, P. K. Das, and S. N. Ege, Can. J. Chem., 62, 424 (1984).
11. 6.
12. -1). In accordance with the theoretical prediction, the kyodai-nitration of bibenzyl gave three isomeric nitro derivatives in a ratio 2-: 3-: 4-nitro = 43 : 5 : 52 in 80% yield at a stage of 64% conversion.
13. E. K. Kim, K. Y. Lee, and J. K. Kochi, J. Am. Chem. Soc., 114, 1756 (1992).
14. For a general survey of aromatic nitration with acetyl nitrate, see: a) G. A. Olah, R. Malhotra, and S. C. Narang, "Nitration, Methods and Mechanisms," VCH Publishers Inc, New York (1989), p. 43;
15. b) K. Schofield, "Aromatic Nitration," Cambridge University Press, London (1980), p. 54.
16. a) C. H. Wu, E. D. Morris, Jr., and H. Niki, J. Phys. Chem., 77, 2507 (1973);
17. b) S. M. Japar and H. Niki, J. Phys. Chem., 79, 1629 (1975);
18. c) R. Atkinson, C. N. Plum, W. P. L. Carter, A. M. Winer, and J. N. Pitts, Jr., J. Phys. Chem., 88, 1210 (1984);
19. d) 88, 4446 (1984).
20. a) H. Suzuki, S. Yonezawa, and T. Mori, Bull Chem. Soc. Jpn., 68, 1535 (1995);
21. b) H. Suzuki, A. Tatsumi, T. Ishibashi, and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1995, 339.