Research on Chemical Intermediates

, Volume 27, Issue 9, pp 975–989

Photooxygenation and photodimerization of 4-methoxystyrene in NaY. The role of co-adsorbed water and alkene–oxygen charge-transfer complex

  • Chie Matsubara
  • Masanobu Kojima
Article

Abstract

On adsorption into NaY, 36% of 4-methoxystyrene (1) was consumed to yield its cis- and trans- chain dimers 2. Irradiation of the NaY sample under vacuum gave cyclic dimers 3, probably through the excimer of 1, and also caused trans-to-cis one-way isomerization of 2. When the NaY sample was irradiated under dry oxygen, 4-methoxybenzaldehyde (4) was given as the major product through photoinduced electron-transfer reaction on excitation of the contact charge-transfer complexes between the guest molecules and O2. The effects of sodium ion and co-adsorbed water on the photodimerization and photooxygenation is also discussed.

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REFERENCES

  1. 1. (a)
    M. Anpo (Ed.), Surface Photochemistry, Vol. 1. Wiley, Chichester (1996)Google Scholar
  2. 1. (b)
    V. Ramamurthy (Ed.), Photochemistry in Organized and Constrained Media. VCH, New York (1991).Google Scholar
  3. 2. (a)
    V. Ramamurthy, D. F. Eaton and J. V. Casper, Acc. Chem. Res. 25, 299 (1992)Google Scholar
  4. 2. (b)
    V. Ramamurthy, Chimia 46, 359 (1992).Google Scholar
  5. 3.
    V. Ramamurthy, J. V. Casper, D. F. Eaton, E. W. Kuo and D. R. Corbin, J. Am. Chem. Soc. 114, 3882 (1992).Google Scholar
  6. 4. (a)
    G. Lem, N. A. Kaprinidis, D. I. Schuster, N. D. Ghatlia and N. J. Turro, J. Am. Chem. Soc. 115, 7009 (1993)Google Scholar
  7. 4. (b)
    V. Ramamurthy, D. R. Corbin, N. J. Turro, Z. Zhang and M. A. Garcia-Garibay, J. Org. Chem. 56, 255 (1991).Google Scholar
  8. 5.
    Y. Kuriyama, H. Takeya, S. Oishi and M. Kojima, Chem. Lett. 843 (1998).Google Scholar
  9. 6.
    H. Garcia, S. Garcia, J. Pérez-Prieto and J. C. Scaiano, J. Phys. Chem. 100, 18158 (1996).Google Scholar
  10. 7.
    V. Ramamurthy, J. V. Casper and D. R. Corbin, J. Am. Chem. Soc. 113, 594 (1991).Google Scholar
  11. 8.
    M. Kojima, H. Takeya, Y. Kuriyama and S. Oishi, Chem. Lett. 997 (1997).Google Scholar
  12. 9. (a)
    V. J. Rao, N. Prevost, V. Ramamurthy, M. Kojima and L. J. Johnston, J. Chem. Soc., Chem. Commun. 2209 (1997)Google Scholar
  13. 9. (b)
    F. L. Cozens, R. Bogdanova, M. Régimbald, H. García, V. Martí and J. C. Scaiano, J. Phys. Chem. B 101, 6921 (1997)Google Scholar
  14. 9. (c)
    V. Fornés, H. García, V. Martí and L. Fernández, Tetrahedron 54, 3827 (1998).Google Scholar
  15. 10. (a)
    T. Hirano, W. Li, L. Abrams, P. J. Krusic, M. F. Ottaviani and N. J. Turro, J. Org. Chem. 65, 1319 (2000)Google Scholar
  16. 10. (b)
    T. Hirano, W. Li, L. Abrams, P. J. Krusic, M. F. Ottaviani and N. J. Turro, J. Am. Chem. Soc. 121, 7170 (1999)Google Scholar
  17. 10. (c)
    S. Jockusch, T. Hirano, Z. Liu and N. J. Turro, J. Phys. Chem. B 104, 1212 (2000).Google Scholar
  18. 11.
    P. S. Lakkaragu, D. Zhou and H. D. Roth, J. Chem. Soc., Chem. Commun. 2605 (1996).Google Scholar
  19. 12. (a)
    F. Blatter and H. Frei, J. Am. Chem. Soc. 115, 7501 (1993)Google Scholar
  20. 12. (b)
    F. Blatter and H. Frei, J. Am. Chem. Soc. 116, 1812 (1994)Google Scholar
  21. 12. (c)
    F. Blatter, F. Moreau and H. Frei, J. Phys. Chem. 98, 13403 (1994)Google Scholar
  22. 12. (d)
    H. Sun, F. Blatter and H. Frei, J. Am. Chem. Soc. 118, 6873 (1996)Google Scholar
  23. 12. (e)
    S. Vasenkov and H. Frei, J. Phys. Chem. B 101, 4539 (1997).Google Scholar
  24. 13. (a)
    M. Kojima, H. Sakuragi and K. Tokumaru, Tetrahedron Lett. 22, 2889 (1981)Google Scholar
  25. 13. (b)
    K. Onodera, G. Furusawa, M. Kojima, M. Tsuchiya, S. Aihara, R. Akaba, H. Sakuragi and K. Tokumaru, Tetrahedron 41, 2215 (1985)Google Scholar
  26. 13. (c)
    M. Kojima, H. Sakuragi and K. Tokumaru, Bull. Chem. Soc. Jpn. 60, 3331 (1987)Google Scholar
  27. 13. (d)
    M. Kojima, H. Sakuragi and K. Tokumaru, Bull. Chem. Soc. Jpn. 62, 3863 (1989)Google Scholar
  28. 13. (e)
    M. Kojima, A. Ishida and S. Takamuku, Chem. Lett. 979 (1993)Google Scholar
  29. 13. (f)
    M. Kojima, A. Ishida and S. Takamuku, Bull. Chem. Soc. Jpn. 71, 2211 (1998).Google Scholar
  30. 14.
    C. Matsubara and M. Kojima, Tetrahedron Lett. 40, 3439 (1999).Google Scholar
  31. 15.
    M. Kojima, A. Odaka, T. Nakajima and Y. Kuriyama, Chem. Lett. 675 (1999).Google Scholar
  32. 16.
    (a) V. Ramamurthy, D. R. Sanderson and D. F. Eaton, J. Am. Chem. Soc. 115, 10438 (1993)Google Scholar
  33. (b).
    V. Ramamurthy, Mol. Cryst. Liq. Cryst. 240, 53 (1994)Google Scholar
  34. (c).
    Z. Zhang, N. J. Turro, L. J. Johnston and V. Ramamurthy, Tetrahedron Lett. 37, 4861 (1996).Google Scholar
  35. 17.
    K.-K. Iu and J. K. Thomas, Langmuir 6, 471 (1990).Google Scholar
  36. 18.
    S. Hashimoto, S. Ikuta, T. Asahi and H. Masuhara, Langmuir 14, 4284 (1998).Google Scholar
  37. 19.
    C.-H. Tung, H. Wang and Y.-M. Ying, J. Am. Chem. Soc. 120, 5179 (1998).Google Scholar
  38. 20. (a)
    J. W. Ward, Advan. Chem. Ser. 102, 380 (1971)Google Scholar
  39. 20. (b)
    J. W. Ward, J. Phys. Chem. 72, 4211 (1968)Google Scholar
  40. 20. (c)
    J. W. Ward, J. Catalysis 10, 34 (1968).Google Scholar
  41. 21. (a)
    D. F. Evans, J. Chem. Soc. 345 (1953)Google Scholar
  42. 21. (b)
    D. F. Evans, J. Chem. Soc. 1351 (1957).Google Scholar
  43. 22.
    H. Tsubomura and R. S. Mulliken, J. Am. Chem. Soc. 82, 5966 (1960).Google Scholar
  44. 23. (a)
    V. I. Stenberg, R. O. Olson, C. T. Wang and N. Kulevsky, J. Org. Chem. 32, 3227 (1967)Google Scholar
  45. 23. (b)
    K. S. Wei and A. H. Adelman, Tetrahedron Lett. 3297 (1969)Google Scholar
  46. 23. (c)
    V. I. Stenberg, C. T. Wang and N. Kulevsky, J. Org. Chem. 35, 1774 (1970)Google Scholar
  47. 23. (d)
    M. Hori, H. Itoi and H. Tsubomura, Bull. Chem. Soc. Jpn. 43, 3765 (1970).Google Scholar
  48. 24.
    Y. S. Park, S. Y. Um and K. B. Yoon, J. Am. Chem. Soc. 121, 3193 (1999).Google Scholar
  49. 25.
    R. Rathore, S. V. Lindeman and J. K. Kochi, J. Am. Chem. Soc. 119, 9393 (1997).Google Scholar
  50. 26.
    H. A. Staab, C. Krieger, P. Wahl and K.-Y. Kay, Chem. Ber. 120, 551 (1987).Google Scholar
  51. 27.
    X. Liu, K.-K. Iu and J. K. Thomas, J. Phys. Chem. 93, 4120 (1989).Google Scholar
  52. 28.
    A. V. Barzkin and S. Hashimoto, J. Chem. Phys. 113, 2841 (2000).Google Scholar
  53. 30.
    H. Al-Ekabi, H. Kawata and P. de Mayo, J. Org. Chem. 53, 1471 (1988).Google Scholar

Copyright information

© VSP 2001 2001

Authors and Affiliations

  • Chie Matsubara
  • Masanobu Kojima

There are no affiliations available

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