Photodimerizations of 1,5- and 1,7-Azulenequinones: Solvent, Substituent, and Concentration Effects on the Product Distribution

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 3, 1998, Pages 711-716

  Kawakami, Hiroko ^a   Van Zhe, Yong ^a   Kato, Nobuo ^a   Mori, Akira ^a   Takeshita, Hitoshi ^b   Nozoe, Tetsuo ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHWA UNIVERSITY   (Japan)

^c KAO CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005895476     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.711     Document Type: Article

References (45)

1. T. Nozoe and H. Takeshita, Bull. Chem. Soc. Jpn., 69, 1149 (1996).
2. T. Nozoe, H. Takeshita, Y. Z. Yan, and A. Mori, Synlett, 1995, 375.
3. H. Takeshita, Y. Z. Yan, N. Kato, A. Mori, and T. Nozoe, Tetrahedron Lett., 36, 5195 (1995).
4. H. Takeshita, Y. Z. Yan, N. Kato, A. Mori, H. Wakabayashi, and T. Nozoe, Tetrahedron Lett., 36, 5199 (1995).
5. [2+4]: a) H. Takeshita, Y. Wada, A. Mori, and T. Hatsui, Chem. Lett., 1973, 335;
6. [4+2]: b) Z.-H. Li, A. Mori, and H. Takeshita, Bull. Chem. Soc. Jpn., 63, 3713 (1990);
7. G. Mehta and S. R. Karra, J. Org. Chem., 54, 2975 (1989);
8. H. Meier, A. Pouli, and H. Kolsorn, Chem. Ber., 122, 101 (1989);
9. e) G. R. Tian, S. Sugiyama, A. Mori, and H. Takeshita, Bull. Chem. Soc. Jpn., 61, 2398 (1988);
10. f) T. Sasaki, T. Manabe, and E. Wakabayashi, Tetrahedron, 36, 2119 (1980);
11. g) K. N. Houk and R. B. Woodward, J. Am. Chem. Soc., 92, 4145 (1970);
12. h) S. Itô, H. Takeshita, and Y. Shoji, Tetrahedron Lett., 1969, 1815;
13. [6+4]: i) D. Forstmeyer, J. Bauer, E. Fontain, R. Herges, R. Herrmann, and I. Ugi, Angew. Chem., Int. Ed. Engl., 27, 1558 (1988);
14. j) S. Itô, Y. Fujise, T. Okuda, and Y. Inoue, Bull. Chem. Soc. Jpn., 39, 1351 (1996);
15. k) R. C. Cookson, B. V. Drake, J. Hudec, and A. Morrison, J. Chem. Soc., Chem. Commun., 1966, 15;
16. [8+2]: l) H. Takeshita, H. Nakashima, S. Sugiyama, and A. Mori, Bull. Chem. Soc. Jpn., 61, 573 (1988);
17. T. S. Cantrell, Tetrahedron Lett., 1975, 907.
18. D. Bryce-Smith and A. Gilbert, J. Chem. Soc., 1964, 2428; E. H. Gold and D. Ginsburg, J. Chem. Soc. C, 1967, 15.
19. D. Bryce-Smith and A. Gilbert, J. Chem. Soc., 1964, 2428; E. H. Gold and D. Ginsburg, J. Chem. Soc. C, 1967, 15.
20. D. Bryce-Smith, A. Gilbert, and M. G. Johnson, J. Chem. Soc. C, 1976, 383.
21. A. Mori and H. Takeshita, Chem. Lett., 1975, 599; A. Mori and H. Takeshita, Bull. Chem. Soc. Jpn., 58, 1581 (1985).
22. A. Mori and H. Takeshita, Chem. Lett., 1975, 599; A. Mori and H. Takeshita, Bull. Chem. Soc. Jpn., 58, 1581 (1985).
23. a) T. Mukai, T. Tezuka, and Y. Akasaki, J. Am. Chem. Soc., 88, 5025 (1966);
24. b) A. S. Kende, J. Am. Chem. Soc., 88, 5026 (1966);
25. T. Tezuka, Y. Akasaki, and T. Mukai, Tetrahedron Lett., 1967, 1397;
26. T. Tezuka, Y. Akasaki, and T. Mukai, Tetrahedron Lett., 1967, 5003;
27. e) I. D. Reingold, K. S. Kwong, and M. M. Menard, J. Org. Chem., 54, 708 (1989);
28. f) A. S. Kende and J. E. Lancaster, J. Am. Chem. Soc., 89, 5283 (1967);
29. g) T. S. Cantrell, J. Am. Chem. Soc., 93, 2540 (1971);
30. h) P. J. Wagner and G. S. Hammond, Adv. Photochem., 5, 23 (1968).
31. A. Mori, H. Kawakami, H. Takeshita, and T. Nozoe, Chem. Lett., 1996, 985.
32. S. Wu, A. Mori, and H. Takeshita, J. Chem. Soc., Chem. Commun., 1994, 919.
33. P. E. Eaton, J. Am. Chem. Soc., 84, 2344 and 2454 (1962); P. E. Eaton and W. S. Hurt, J. Am. Chem. Soc., 88, 5038 (1966).
34. P. E. Eaton, J. Am. Chem. Soc., 84, 2344 and 2454 (1962); P. E. Eaton and W. S. Hurt, J. Am. Chem. Soc., 88, 5038 (1966).
35. R. Reinfried, D. Bellus, and K. Schaffner, Helv. Chim. Acta, 54, 1517 (1971).
36. K.-H. Lee and P. de Mayo, J. Chem. Soc., Chem. Commun., 1979, 493.
37. G. Lem, N. A. Karprinidis, D. I. Schuster, N. D. Ghatlia, and N. J. Turro, J. Am. Chem. Soc., 115, 7009 (1993).
38. E. Y. Y. Lam, D. Valentine, and G. S. Hammond, J. Am. Chem. Soc., 89, 3482 (1967).
39. P. J. Wagner and D. J. Bucheck, J. Am. Chem. Soc., 91, 5090 (1969).
40. J. L. Ruhlen and P. A. Learmakers, J. Am. Chem. Soc., 89, 4944 (1967).
41. When 6 was counted as a product from an HT dimer, the ratio of the HH and HT dimers decreased from 0.6 to 0.3.
42. Intermediates 11 and 12 might be mutually convertible via a [5,5] sigmatropy under the conditions.
43. Tables of fractional atomic coordinates and equivalent isotropic displacement parameters and geometric parameters including interatomic bond distances and angles for 1 are deposited as Document No. 71013 at the Office of Editor of Bull. Chem. Soc. Jpn.
44. M. C. Altomare, M. Burla, G. Camalli, C. Cascarano, A. Giacovazzo, G. Guagliardi, and J. Polidori, J. Appl. Crystallogr., 27, 435 (1994).
45. G. M. Sheldrick, "Program for the Refinement of Crystal Structure," University of Göttingen, Germany (1993).