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Photoreactions of (2-Alkoxymethylphenyl)pentamethyldisilanes

  • Park, Seung-Ki (Department of Chemistry, College of Natural Sciences, The University of Suwon)
  • Published : 2006.09.20
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Abstract

Photolysis of (2-hydroxymethylphenyl)pentamethyldisilane 1 in methanol provides a novel intramolecular photoproduct 4 via silene intermediate 2 but the photoreaction of (2-acetoxymethyl- or allyloxymethylphenyl) pentamethyldisilanes 5 or 10 in methanol affords unexpected photoproducts 8 or 13, respectively, instead of expected intramolecular photoproducts.

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References

  1. Ishikawa, M.; Fuchikami, T.; Sugaya, T.; Kumada, M. J. Am. Chem. Soc. 1975, 97, 5923 https://doi.org/10.1021/ja00853a052
  2. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1976, 118, 155 https://doi.org/10.1016/S0022-328X(00)92150-8
  3. Morkin, T. L.; Leigh, W. J. Acc. Chem. Res. 2001, 34, 129 https://doi.org/10.1021/ar960252y
  4. Leigh, W. J.; Sluggett, G. W. J. Am. Chem. Soc. 1994, 116, 10468
  5. Steinmetz, M. G. Chem. Rev. 1995, 95, 1527 https://doi.org/10.1021/cr00037a017
  6. Nate, K.; Ishikawa, M.; Ni, H.; Watanabe, H.; Saheki, Y. Organometallics 1987, 6, 1673 https://doi.org/10.1021/om00151a011
  7. Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Minato, A. Organometallics 1991, 10, 880 https://doi.org/10.1021/om00050a016
  8. Takaki, K.; Sakamoto, H.; Nishimura, Y.; Sugihara, Y.; Ishikawa, M. Organometallics 1991, 10, 888 https://doi.org/10.1021/om00050a017
  9. Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Tsukihara, T.; Takahashi, K.; Kiso, Y. Organometallics 1991, 10, 2685 https://doi.org/10.1021/om00054a033
  10. Ishikawa, M.; Nishimura, Y.; Sakamoto, H. Organometallics 1991, 10, 2701 https://doi.org/10.1021/om00054a035
  11. Kira, M.; Miyazawa, T.; Sugiyama, H.; Yamaguchi, M.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 3116 https://doi.org/10.1021/ja00061a010
  12. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1977, 133, 19 https://doi.org/10.1016/S0022-328X(00)98113-0
  13. Ohshita, J.; Niwa, H.; Ishikawa, M. Organometallics 1996, 15, 4632 https://doi.org/10.1021/om960259j
  14. Toltl, N. P.; Leigh, W. J. Organometallics 1996, 15, 2554 https://doi.org/10.1021/om960011u
  15. Leigh, W. J.; Sluggett, G. W. Organometallics 1994, 13, 269 https://doi.org/10.1021/om00013a040
  16. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1976, 118, 139 https://doi.org/10.1016/S0022-328X(00)92149-1
  17. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1978, 162, 223 https://doi.org/10.1016/S0022-328X(00)82040-9
  18. Ishikawa, M.; Sakamoto, H.; Kanetani, F.; Minato, A. Organometallics 1989, 8, 2767 https://doi.org/10.1021/om00114a005
  19. Sakurai, H. J. Organomet. Chem. 1980, 200, 261 https://doi.org/10.1016/S0022-328X(00)88650-7
  20. Guselnikov, L. E.; Nametkin, N. S. Chem. Rev. 1979, 79, 529 https://doi.org/10.1021/cr60322a004
  21. Ohshita, J.; Niwa, H.; Ishikawa, M.; Yamabe, T.; Yoshii, T.; Nakamura, K. J. Am. Chem. Soc. 1996, 118, 6853 https://doi.org/10.1021/ja960458u
  22. Ishikawa, M.; Oda, M.; Miyoshi, N.; Fabry, L.; Kumada, M.; Yamabe, T.; Akagi, K.; Fukui, K. J. Am. Chem. Soc. 1979, 101, 4612 https://doi.org/10.1021/ja00510a028
  23. Ohshita, J.; Ohsaki, H.; Ishikawa, M. Organometallics 1991, 10, 2695 https://doi.org/10.1021/om00054a034
  24. Sakurai, H.; Nakadaira, Y.; Kira, M.; Sugiyama, H.; Yoshida, K.; Takiguchi, T. J. Organomet. Chem. 1980, 184, C36 https://doi.org/10.1016/S0022-328X(00)83499-3
  25. shikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1977, 127, 261 https://doi.org/10.1016/S0022-328X(00)89716-8
  26. Ishikawa, M.; Kikuchi, M.; Kunai, A.; Takeuchi, T.; Tsukihara, T.; Kido, M. Organometallics 1993, 12, 3474 https://doi.org/10.1021/om00033a018
  27. Ishikawa, M.; Kikuchi, M.; Watanabe, K.; Sakamoto, H.; Kunai, A. J. Organomet. Chem. 1993, 443, C3 https://doi.org/10.1016/0022-328X(93)80022-4
  28. Park, S. K.; Baek, D. J. J. Photochem. Photobiol. A: Chem. 2004, 163, 87 and references cited therein https://doi.org/10.1016/S1010-6030(03)00440-4
  29. Park, S. K. J. Photochem. Photobiol. A: Chem. 2005, 173, 29 https://doi.org/10.1016/j.jphotochem.2004.11.020
  30. Hijji, Y. M.; Hudrlik, P. F.; Okoro, C. O.; Hudrlik, A. M. Syn. Commun. 1997, 27, 4297 https://doi.org/10.1080/00397919708005053
  31. Park, S. K.; Shim, S. C. J. Photochem. Photobiol. A: Chem. 2000, 136, 219 https://doi.org/10.1016/S1010-6030(00)00323-3
  32. Ishikawa, M.; Shirai, S.; Naka, A.; Kobayashi, H.; Ohshita, J.; Kunai, A.; Yamamoto, Y.; Cha, S. H.; Lee, K. K.; Kwak, Y. W. Organometallics 2002, 21, 4206 https://doi.org/10.1021/om020316a
  33. Ishikawa, M.; Sakamoto, H. J. Organomet. Chem. 1991, 414, 1

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