N-Hydroxyphthalimide (NHPI)-catalyzed reaction of adamantane under nitric oxide atmosphere

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7075-7078

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

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030819608     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01652-3     Document Type: Article

References (33)

1. (a) Becker, P. N.; White, M. A.; Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5676-5677.
2. (b) Okamoto, T,; Kobayashi, K.; Oka, S.; Tanimoto, S. J. Org. Chem. 1987, 52, 5089-5092.
3. (c) Palmer, R. M.; Ferrige, A, G,: Moncada, S. Nature, 1987, 327, 524-526.
4. (d) Garthwaite, J.; Chrles, S. L.; Chess-Willams, R. Nature, 1988, 336, 385-388.
5. (e) Stander, J. L.; Lodscalzo, J. Science, 1992, 258, 1898-1902.
6. (f) Feldman, P. L.; Griffith, O, W.; Stuehr, D. J. Chem. Eng. News, 1993, 26-38.
7. (g) Wilcox, A. L.; Janzen, E. G. J. Chem. Soc., Chem. Comm. 1993, 1377-1379.
8. (h) Janzen, E. G.; Wilcox, A. L.; Manoharan, V. J. Org. Chem. 1993, 58, 3597-3599.
9. (i) de la Breteche, M.-L.; Servy, C.; Lenfant, M.; Ducrocq, C. Tetrahedron Lett. 1994, 35, 7231-7232.
10. (j) Itoh, T.; Nagata, K.; Okada, M.; Ohsawa, A. Tetrahedron Lett. 1995, 36, 2269-2272.
11. (k) Nagano, T.; Takizawa, H.; Hirobe, M. Tetrahedron Lett. 1995, 36, 8239-8242.
12. (l) Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3629-3636.
13. (m) Itoh, T.; Nagata, K.; Matsuya, Y.; Miyazaki, M.; Ohsawa, A. J. Org. Chem. 1997, 62, 3582-3585.
14. (a) Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319-1329.
15. (b) Bosch, E.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 1, 1996, 2731-2738.
16. (c) Suzuki, H.; Yonezawa, S.; Nonoyama, N.; Mori, T. J. Chem. Soc., Perkin Trans. 1, 1996, 2385-2389, and references cited therein.
17. Groves, J. T.; Roman, S. J. Am. Chem. Soc. 1995, 117, 5594-5595.
18. Suzuki, H.; Nonoyama, N. Chem. Commun. 1996, 1783-1784.
19. Ishii, Y.; Kato, S.; Iwahama, T.; Sakaguchi, S. Tetrahedron Lett. 1996, 37, 4993-4996.
20. 7 151-152 °C).
21. Kretzberger. A.; Schröders, H.-H. Tetrahedron Lett. 1970, 4523-4526.
22. (a) Koch, V. R.; Miller, L. L. J. Am. Chem. Soc. 1973, 95, 8631-8637.
23. (b) Olah, G. A.; Ramaiah, P.; Rao, C. B.; Sandford, G.; Golam, R.; Trivedi, N. J.; Olah, J. A. J. Am. Chem. Soc. 1993, 115, 7246-7249.
24. Traylor, T. G.; Sharma, V. S. Biochemistry, 1992, 31, 2847-2849.
25. (a) Walling, C. Free Radicals in Solution, Wiley, New York, 1957.
26. (b) Wagniére, G. H. The chemistry of the nitro and nitroso groups, Part 1, Fewer, H. Ed., New York, 1969, pp 7-10.
27. (c) Kochi, J. K. Free Radicals, Wiley, New York, 1973, vol. II.
28. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyma, Y. J. Org. Chem. 1996, 61, 4520-4526.
29. Macker, A.; Wajer, A. J. W.; de Boer, J. Tetrahedron, 1968, 24, 1623-1631.
30. -1 M NHPI was exposed under an NO atmosphere at 100 °C for 30 min.
31. Nappa, M. J.; Tolman, C. A. Inorg. Chem. 1985, 24, 4711-4719.
32. (a) Smegal, J. A.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3515-3521.
33. (b) Renneke, R. F.; Hill, C. L. J. Am. Chem. Soc. 1986, 108, 3528-3529.