9,10-Dicyanoanthracene-photosensitized elimination of 1,1'-binaphthalene from dinaphthyl methylphosphonate and trinaphthyl phosphate through the termolecular interaction in the singlet excited state

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 9, 1999, Pages 2103-2109

  Nakamura, Mitsunobu ^a   Miki, Masamichi ^a   Majima, Tetsuro ^b  

^a UNIVERSITY OF HYOGO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; METHYLPHOSPHONIC ACID; NAPHTHALENE DERIVATIVE; PHOSPHORUS DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON TRANSPORT; MOLECULAR INTERACTION; PHOTOSENSITIZATION; POLARIZATION; SPECTRAL SENSITIVITY;

EID: 0032874754     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.2103     Document Type: Article

References (26)

1. For example, see: M. Shi and Y. Inoue, J. Chem. Soc., Perkin Trans. 2, 1998, 2421; S. Jockusch, I. V. Koptyug, P. F. McGarry, G. W. Sluggett, N. J. Turro, and D. M. Watkins, J. Am. Chem. Soc., 119, 11495 (1997); G. Pandey, S. Hajra, M. K. Ghorai, and K. R. Kumar, J. Am. Chem. Soc., 119, 8777 (1997); H. Tomioka and Y. Izawa, Yuki Gosei Kagaku Kyoukaishi, 34, 901 (1976), and references cited therein.
2. For example, see: M. Shi and Y. Inoue, J. Chem. Soc., Perkin Trans. 2, 1998, 2421; S. Jockusch, I. V. Koptyug, P. F. McGarry, G. W. Sluggett, N. J. Turro, and D. M. Watkins, J. Am. Chem. Soc., 119, 11495 (1997); G. Pandey, S. Hajra, M. K. Ghorai, and K. R. Kumar, J. Am. Chem. Soc., 119, 8777 (1997); H. Tomioka and Y. Izawa, Yuki Gosei Kagaku Kyoukaishi, 34, 901 (1976), and references cited therein.
3. For example, see: M. Shi and Y. Inoue, J. Chem. Soc., Perkin Trans. 2, 1998, 2421; S. Jockusch, I. V. Koptyug, P. F. McGarry, G. W. Sluggett, N. J. Turro, and D. M. Watkins, J. Am. Chem. Soc., 119, 11495 (1997); G. Pandey, S. Hajra, M. K. Ghorai, and K. R. Kumar, J. Am. Chem. Soc., 119, 8777 (1997); H. Tomioka and Y. Izawa, Yuki Gosei Kagaku Kyoukaishi, 34, 901 (1976), and references cited therein.
4. For example, see: M. Shi and Y. Inoue, J. Chem. Soc., Perkin Trans. 2, 1998, 2421; S. Jockusch, I. V. Koptyug, P. F. McGarry, G. W. Sluggett, N. J. Turro, and D. M. Watkins, J. Am. Chem. Soc., 119, 11495 (1997); G. Pandey, S. Hajra, M. K. Ghorai, and K. R. Kumar, J. Am. Chem. Soc., 119, 8777 (1997); H. Tomioka and Y. Izawa, Yuki Gosei Kagaku Kyoukaishi, 34, 901 (1976), and references cited therein.
5. For example, see: S. Steenken and L. Goldbergerova, J. Am. Chem. Soc., 120, 3928 (1998); R. S. Givens, P. S. Athey, B. Matuzewski, L. W. Kuepper, III, J.-y. Xue, and T. Fister, J. Am. Chem. Soc., 115, 6001 (1993); M. C. Pirrung and S. W. Shuey, J. Org. Chem., 59, 3890 (1994); T. Furuta, H. Torigai, M. Sugimoto, and M. Iwamura, J. Org. Chem., 60, 3953 (1995); R. S. Givens and L. W. Kuepper, III, Chem. Rev., 93, 55 (1993), and references cited therein.
6. For example, see: S. Steenken and L. Goldbergerova, J. Am. Chem. Soc., 120, 3928 (1998); R. S. Givens, P. S. Athey, B. Matuzewski, L. W. Kuepper, III, J.-y. Xue, and T. Fister, J. Am. Chem. Soc., 115, 6001 (1993); M. C. Pirrung and S. W. Shuey, J. Org. Chem., 59, 3890 (1994); T. Furuta, H. Torigai, M. Sugimoto, and M. Iwamura, J. Org. Chem., 60, 3953 (1995); R. S. Givens and L. W. Kuepper, III, Chem. Rev., 93, 55 (1993), and references cited therein.
7. For example, see: S. Steenken and L. Goldbergerova, J. Am. Chem. Soc., 120, 3928 (1998); R. S. Givens, P. S. Athey, B. Matuzewski, L. W. Kuepper, III, J.-y. Xue, and T. Fister, J. Am. Chem. Soc., 115, 6001 (1993); M. C. Pirrung and S. W. Shuey, J. Org. Chem., 59, 3890 (1994); T. Furuta, H. Torigai, M. Sugimoto, and M. Iwamura, J. Org. Chem., 60, 3953 (1995); R. S. Givens and L. W. Kuepper, III, Chem. Rev., 93, 55 (1993), and references cited therein.
8. For example, see: S. Steenken and L. Goldbergerova, J. Am. Chem. Soc., 120, 3928 (1998); R. S. Givens, P. S. Athey, B. Matuzewski, L. W. Kuepper, III, J.-y. Xue, and T. Fister, J. Am. Chem. Soc., 115, 6001 (1993); M. C. Pirrung and S. W. Shuey, J. Org. Chem., 59, 3890 (1994); T. Furuta, H. Torigai, M. Sugimoto, and M. Iwamura, J. Org. Chem., 60, 3953 (1995); R. S. Givens and L. W. Kuepper, III, Chem. Rev., 93, 55 (1993), and references cited therein.
9. For example, see: S. Steenken and L. Goldbergerova, J. Am. Chem. Soc., 120, 3928 (1998); R. S. Givens, P. S. Athey, B. Matuzewski, L. W. Kuepper, III, J.-y. Xue, and T. Fister, J. Am. Chem. Soc., 115, 6001 (1993); M. C. Pirrung and S. W. Shuey, J. Org. Chem., 59, 3890 (1994); T. Furuta, H. Torigai, M. Sugimoto, and M. Iwamura, J. Org. Chem., 60, 3953 (1995); R. S. Givens and L. W. Kuepper, III, Chem. Rev., 93, 55 (1993), and references cited therein.
10. Ya. A. Levin, A. V. Il'yason, E. I. Gol'dfarb, and A. Sh. Mukhtarov, Sb. Nek. Probl. Org. Khim., Mater. Nauchn. Sess., Inst. Org. Fiz. Khim., Akad. Nauk SSSR, 1972, 201;
11. c) H. Tomioka, Y. Hirano, and Y. Izawa, Tetrahedron Lett., 1974, 1865.
12. a) R. A. Finnegan and J. A. Maston, J. Am. Chem. Soc., 94, 4780 (1975).
13. b) M. Nakamura, K. Sawasaki, Y. Okamoto, and S. Takamuku, Bull. Chem. Soc. Jpn., 68, 3189 (1995).
14. c) M. Nakamura, R. Dohno, and T. Majima, Chem. Commun., 1997, 1291.
15. d) M. Nakamura, R. Dohno, and T. Majima, J. Org. Chem., 63, 6258 (1998).
16. E. Hasegawa, K. Okada, and T. Mukai, J. Am. Chem. Soc., 106, 6852 (1984); E. Hasegawa, K. Okada, H. Ikeda, Y. Yamashita, and T. Mukai, J. Org. Chem., 56, 2170 (1991).
17. E. Hasegawa, K. Okada, and T. Mukai, J. Am. Chem. Soc., 106, 6852 (1984); E. Hasegawa, K. Okada, H. Ikeda, Y. Yamashita, and T. Mukai, J. Org. Chem., 56, 2170 (1991).
18. 1DCA* and 1 is not involved in the binaphthalene elimination in benzene.
19. H. Hirayama, J. Chem. Phys., 42, 4163 (1965).
20. H. Beens and A. Weller, Chem. Phys. Lett., 2, 140 (1968).
21. H. Itagaki, N. Obutaka, A. Okamoto, K. Horie, and I. Mita, Chem. Phys. Lett., 78, 143 (1981); H. Itagaki, N. Obutaka, A. Okamoto, K. Horie, and I. Mita, J. Am. Chem. Soc., 104, 4469 (1982).
22. H. Itagaki, N. Obutaka, A. Okamoto, K. Horie, and I. Mita, Chem. Phys. Lett., 78, 143 (1981); H. Itagaki, N. Obutaka, A. Okamoto, K. Horie, and I. Mita, J. Am. Chem. Soc., 104, 4469 (1982).
23. K. Sasse, "Methoden der Organischen Chimie, XII/1 Organische Phosphorverbindungen," ed by E. Muller, Thieme Verlag, Stuttgart (1963), Vol. 1, p. 339.
24. E. W. Dehmlow and J. Schmidt, Tetrahedron Lett., 1976, 15.
25. W. M. Moore, G. S. Hammond, and R. P. Foss, J. Am. Chem. Soc., 83, 2789 (1961); W. M. Moore and M. Ketchum, J. Am. Chem. Soc., 84, 1368 (1962).
26. W. M. Moore, G. S. Hammond, and R. P. Foss, J. Am. Chem. Soc., 83, 2789 (1961); W. M. Moore and M. Ketchum, J. Am. Chem. Soc., 84, 1368 (1962).