Conformational specificity in photoinduced intramolecular 1,7-hydrogen abstraction of homonaphthoquinones with a spiro-linked dibenzocycloheptene ring

Organic Letters

Volumn 2, Issue 4, 2000, Pages 559-561

  Kokubo, Ken ^a   Kawahara, Kazuhito ^a   Takatani, Toshihiko ^a   Moriwaki, Hiroshi ^a   Kawamoto, Tatsuya ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000005565     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005520d     Document Type: Article

References (39)

1. (a) Wagner, P. J.; Park, B.-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker, Inc.: New York, 1991; Volume 11, Chapter 4, p 227.
2. (b) Wagner, P. J. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, 1995; Chapter 38, p 449.
3. (a) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168.
4. (b) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
5. (c) Dorigo, A. E.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 2195.
6. (d) Dorigo, A. E.; McCarriek, M. A.; Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 7508.
7. (e) Sengupta, D.; Sumathi, R.; Chandra, A. K. J. Photochem. Photobiol. A: Chem. 1991, 60, 149.
8. (f) Griesbeck, A. G.; Heckroth, H.; Lex, J. Chem. Commun. 1999, 1109.
9. (a) Descotes, G. L. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, 1995; Chapter 41, p 501. See also recent papers:
10. (b) Kerwin, S. M.; Heathcock, C. H. J. Org. Chem. 1992, 57, 4005.
11. (c) Hasegawa, T.; Takahashi, K.; Aoyama, H.; Yoshioka, M. Bull. Chem. Soc. Jpn. 1992, 65, 3498.
12. (d) Kraus, G. A.; Zhang, W.; Wu, Y. Chem. Commun. 1996, 2439.
13. (e) Leigh, W. L.; Lathioor, E. C.; St. Pierre, M. J. J. Am. Chem. Soc. 1996, 118, 12339.
14. (f) Hu, S.; Neckers, D. C. J. Chem. Soc., Perkin Trans. 2 1997, 1751.
15. (g) Hu, S.; Neckers, D. J. Org. Chem. 1997, 62, 6820.
16. (h) Mizuno, K.; Konishi, S.; Yoshimi, Y.; Sugimoto, A. Chem. Commun. 1998, 1659.
17. (i) Jung, M. E.; Johnson, T. W. J. Org. Chem. 1999, 64, 7651.
18. (j) Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem., Int. Ed. 1999, 38, 2583.
19. (a) Toda, F.; Yagi, M.; Soda, S. J. Chem. Soc., Chem. Commun. 1987, 1413.
20. (b) Sakamoto, M.; Takahashi, M.; Fujita, T.; Nishio, T.: Iida, I.; Watanabe, S. J. Org. Chem. 1995, 60, 4682.
21. (c) Irngartinger, H.; Fettel, P. W.; Siemund, V. Eur. J. Org. Chem. 1998, 2079.
22. (d) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755.
23. (a) Scheffer, J. R.; Dzakpasu, A. A. J. Am. Chem. Soc. 1978, 100, 2163.
24. (b) Ariel, S.; Askari, S.; Scheffer, J. R.; Trotter, J. J. Org. Chem. 1989, 54, 4324.
25. (c) Gudmundsdottir, A. D.; Lewis, T. J.; Randall, L. H.; Scheffer, J. R.; Rettig, S. J.; Trotter, J.; Wu, C.-H. J. Am. Chem. Soc. 1996, 118, 6167.
26. (d) Ito, Y.; Yasui, S.; Yamauchi, J.; Ohba, S.; Kano, G. J. Phys. Chem. A 1998, 102, 5415 and ref 4d.
27. Oshima, T.; Fujii, S.; Takatani, T.; Kokubo, K.; Kawamoto, T. J. Chem. Soc., Perkin Trans. 2 1999, 1783.
28. Tamura, H.; Oshima, T.; Matsubayashi, G.; Nagai, T. Acta Crystallogr. 1995, C51, 1148.
29. w = 0.070 for 1672 reflections with I > 1.5σ(I).
30. For example: (a) Carless, H. A. J.; Fekarurhobo, G. K. Tetrahedron Lett. 1984, 25, 5943.
31. (b) Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Chem. Commun. 1985, 1381.
32. (c) Zhou, B.; Wagner, P. J. J. Am. Chem. Soc. 1989, 111, 6796.
33. (d) Sauers, R. R.; Huang, S.-Y. Tetrahedron Lett. 1990, 31, 5709.
34. Unfortunately, at present, the position of photochemical equilibration was not determined due to the preferential photocyclization of α-conformer.
35. 3, Z = 8, R = 0.062 and Rw = 0.064 tor 4895 reflections with I > 2.00σ(I).
36. Calculations using the PM3 method were performed with the CS MOPAC Pro program (version 4.0) using CS Chem3D Pro software, CambridgeSoft Co.
37. Since the hydrogen abstraction is generally known to occur from the excited triplet state in the case of carbonyl compounds, geometrical parameters for the lowest triplet states were also calculated. However, the structural relaxation for the excited state is so small that the triplet structure essentially resembles the ground state (within a deviation of ±0.02 Å for d, and ±0.6° for other angles).
38. For a recent paper in which the semiempirical calculation is also applied to the geometrical parameters for the Norrish type II reaction, see: Griesbeck, A. G.; Henz, A.; Kramer, W.; Wamser, P. Tetrahedron Lett. 1998, 39, 1549 and ref 8d.
39. Sauers, R. R.; Scimone, A.; Shams, H. J. Org. Chem. 1988, 53, 6084.