Direct Oxidation of Methyl Ethers to Carbonyl Compounds with a Combination of Nitrogen Dioxide and Water in the Presence or Absence of Ozone

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 12, 1997, Pages 3111-3115

  Suzuki, Hitomi ^a   Takeuchi, Toyomi ^a   Mori, Tadashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013199737     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.3111     Document Type: Article

References (32)

1. For aromatic nitration using nitrogen dioxide and ozone, see: a) T. Mori and H. Suzuki, Synlett, 1995, 383; b) T. Mori, Ph. D. Thesis, Kyoto University, 1997. Electronic version of this thesis is available via WWW: (http://kuchem.kyoto-u.ac.jp/www/yugo/user/tmori/th/cont.html).
2. For aromatic nitration using nitrogen dioxide and ozone, see: a) T. Mori and H. Suzuki, Synlett, 1995, 383; b) T. Mori, Ph. D. Thesis, Kyoto University, 1997. Electronic version of this thesis is available via WWW: (http://kuchem.kyoto-u.ac.jp/www/yugo/user/tmori/th/cont.html).
3. a) H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1997, 1265;
4. b) H. Suzuki and T. Mori, Chem. Lett., 1996, 647;
5. c) H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1996, 677;
6. d) H. Suzuki, S. Yonezawa, and T. Mori, Bull. Chem. Soc. Jpn., 68, 1535 (1995);
7. e) H. Suzuki, A. Tatsumi, T. Ishibashi, and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1995, 339;
8. f) H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1994, 479;
9. g) H. Suzuki and T. Mori, J. Chem. Soc., Chem. Commun., 1994, 1443.
10. a) H. Suzuki, T. Murashima, I. Kozai, and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1993, 1591;
11. b) H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1995, 291.
12. I. T. Harrison and S. Harrison, J. Chem. Soc., Chem. Commun., 1966, 752.
13. G. A. Olah, B. G. B. Gupta, and A. P. Fung, Synthesis, 1980, 897.
14. C. D. Synder and H. Rapoport, J. Am. Chem. Soc., 94, 227 (1972).
15. a) T. Nishiguchi and M. Bougauchi, J. Org. Chem., 54, 3001 (1989);
16. b) Also see: T. Nishiguchi and F. Asano, J. Org. Chem., 54, 1531 (1989).
17. a) G. A. Olah and J. Welch, J. Am. Chem. Soc., 100, 5396 (1978);
18. b) G. A. Olah, J. Welch, and T.-L. Ho, J. Am. Chem. Soc., 98, 6717 (1976).
19. O. C. Musgrave, Chem. Rev., 69, 499 (1969).
20. a) D. H. R. Barton, P. D. Magnus, G. Streckert, and D. Zurr, J. Chem. Soc., Chem. Commun., 1971, 1109;
21. b) M. E. Jung and L. M. Speltz, J. Am. Chem. Soc., 98, 7882 (1976).
22. T.-L. Ho and G. A. Olah, J. Org. Chem., 42, 3097 (1977).
23. G. A. Olah and T.-L. Ho, Synthesis, 1976, 609.
24. a) T. Shono, Y. Yamamoto, and K. Takigawa, Chem. Lett., 1994, 1045;
25. b) Also see: H. Suzuki and N. Nonoyama, J. Chem. Soc., Chem. Commun., 1996, 1783.
26. a) M. M. Rogic, J. Vitrone, and M. D. Swerdloff, J. Am. Chem. Soc., 99, 1156 (1977);
27. b) J. Am. Chem. Soc., 97, 3848 (1975).
28. L. Eberson, M. P. Hartshorn, O. Persson, and F. Radner, J. Chem. Soc., Chem. Commun., 1996, 2105, and references cited therein.
29. B. A. Stoochnoff and N. L. Benoiton, Tetrahedron Lett., 1973, 21.
30. J. L. Holcombe and T. Livinghouse, J. Org. Chem., 51, 111 (1986).
31. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 94, 6190 (1972).
32. K. Fukase, H. Tanaka, S. Torii, and S. Kusumoto, Tetrahedron Lett., 31, 389 (1990).