A new approach for oxygenation using nitric oxide under the influence of N-hydroxyphthalimide

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4676-4679

  Eikawa, Masahiro ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ISOCHROMAN DERIVATIVE; NITRIC OXIDE; PHTHALALDEHYDE; PHTHALIMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; OXYGENATION; REACTION ANALYSIS;

EID: 0033603614     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982406o     Document Type: Article

References (28)

1. (a)Walling, C. Free Radicals in Solution; Wiley: New York, 1957.
2. (b) Kochi, J. K. Free Radicals; Wiley: New York, 1973; Vol. II.
3. (c) Jones, K. Comprehensive Inorganic Chemistry, Vol. 2; Trotman-Dickenson, A. F., Ed.; Pergamon Press: Oxford, 1973.
4. Culotta, E.; Koshland, D. E., Jr. Science 1992, 258, 1862.
5. Wrightham, M. N.; Cann, A. J.; Sewel, H. F. Med. Hypotheses 1992, 38, 236.
6. (a) Kato, K.; Mukaiyama, T. Chem. Lett. 1990, 1395.
7. (b) Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3629 and references therein.
8. (a) Nagano, T.; Takizawa, H.; Hirobe, M. Tetrahedron Lett. 1995, 36, 8239.
9. (b) Itoh, T.; Nagata, K.; Matsuya, Y.; Miyazaki, M.; Ohsawa, A. J. Org. Chem. 1997, 62, 3582 and references therein,
10. (c) Bosch, E.; Kochi, J. K J. Chem. Soc., Perkin Tarans. 1 1995, 1057.
11. (d) Park, J. S. B.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1997, 2579.
12. (a) Sakaguchi, S.; Takase, T.; Iwahama, T.; Ishii, Y. Chem. Commun. 1998, 2037.
13. (b) Sakaguchi, S.; Kato, S.; Iwahama, T.; Ishii, Y. Bull. Chem. Soc. Jpn. 1998, 71, 1, 1237.
14. (c) Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810.
15. (d) Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 67, 4520.
16. Sakaguchi, S.; Eikawa, M.; Ishii, Y. Teatrahedron Lett. 1997, 38, 7075.
17. (a) Cha, J. S.; Lee, K. D.; Kwon, O. O.; Kim, J. M.; Lee, H. S. Bull. Korean. Chem. Soc. 1995, 16, 561.
18. (b) Corriu, R. J. P.; Lanneau, G. F.; Perrot, M. Tetrahedron Lett. 1988, 29, 1271.
19. (c) Firouzabadi, H.; Iranpoor, N.; Kiaeezadeh, F.; Toofan, J. Tetrahedron 1986, 42, 719.
20. (d) Green, G.; Griffith, A. P.; Hollinshead, D. M.; Ley, S. V.; Schršder, M. J. Chem. Soc., Perkin Trans. 1 1984, 681.
21. (e) Ariyoshi, K.; Aso, Y.; Otsubo, T.; Ogura, F. Chem. Lett. 1984, 891.
22. Bill, J. C.; Tarbell, D. S. Organic Syntheses, Collect. Vol. IV; Wiley: New York, 1963; p 807.
23. 4 was found to exist in equilibrium with cyclic hemiacetal form 2-(hydroxymethyl)benzaldehyde by NMR measurement. Harron, J.; McClellnad, R. A.; Thankachan, C.; Tidwell, T. T. J. Org. Chem. 1981, 46, 903.
24. Absolute acetonitrile containing water (<0.005%) was purchased from Wako Pure Chemical Industries, Ltd.
25. Xu, Y.-C.; Lebeau, E.; Gillard, J. W.; Attardo, G. Tetrahedron Lett. 1993, 34, 3841.
26. Yamato, M.; Hashigaki, K; Yasumoto, Y.; Sakai, J.; Luduena, R. F.; Banerjee, A.; Tsukagoshi, S.; Tashiro, T.; Tsuruo, T. J. Med. Chem. 1987, 30, 1897 and references therein.
27. Wilcox, A. L.; Janzen, E. G. J. Chem. Soc., Chem. Commun. 1993, 1377.
28. Suzuki, H. Pharmacia 1997, 33, 487.