Bulletin of the Korean Chemical Society

  • 제30권6호
  • /
  • Pages.1331-1336
  • /
  • 2009
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

A Novel Photoreaction of (2-Hydroxyethoxyphenyl)pentamethyldisilane

  • Park, Seung Ki (Department of Chemistry, College of Natural Sciences, The University of Suwon) ;
  • Seong, Won-Je (Department of Chemistry, College of Natural Sciences, The University of Suwon)
  • 발행 : 2009.06.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Photolysis of (2-hydroxyethoxyphenyl)pentamethyldisilane 2 in benzene provides a novel intramolecular cyclization photoproduct 9 which was probably formed from the intramolecular reaction to form a seven-membered ring in silatriene intermediate 7 and then the photochemical disrotatory ring closure of 1,3-butadiene moiety to cyclobutene. Irradiation of 2 in methanol afforded photoproducts 5 and 6 which were formed by the nucleophilic attack of methanol to $\beta$ or $\alpha$ silicon atom in pentamethyldisilanyl group of the photoexcited state of 2. Compounds 10 and 11 were also formed by the same way as in the formation of the photoproducts 5 and 6 in the photolysis of (2-allyloxyethoxyphenyl)pentamethyldisilane 3 in methanol solvent. Photoreaction of (2-acetoxyethoxyphenyl) pentamethyldisilane 4 in methanol gave a photoproduct 12 which was formed via the elimination of dimethylsilylene species in the photoexcited state of 4.

키워드

참고문헌

  1. Ishikawa, M.; Fuchikami, T.; Sugaya, T.; Kumada, M. J. Am. Chem. Soc. 1975, 97, 5923. https://doi.org/10.1021/ja00853a052
  2. Nate, K.; Ishikawa, M.; Ni, H.; Watanabe, H.; Saheki, Y. Organometallics 1987, 6, 1673. https://doi.org/10.1021/om00151a011
  3. Ishikawa, M. Pure Appl. Chem. 1978, 50, 11. https://doi.org/10.1351/pac197850010011
  4. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1976, 118, 139. https://doi.org/10.1016/S0022-328X(00)92149-1
  5. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1976, 118, 155. https://doi.org/10.1016/S0022-328X(00)92150-8
  6. Ishikawa, M.; Fuchikami, T.; Kumada, M. Tetrahedron Lett. 1976, 1299.
  7. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem.1977, 133, 19. https://doi.org/10.1016/S0022-328X(00)98113-0
  8. Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1978, 162, 223. https://doi.org/10.1016/S0022-328X(00)82040-9
  9. 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
  10. Ishikawa, M.; Oda, M.; Nishimura, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1983, 56, 2795. https://doi.org/10.1246/bcsj.56.2795
  11. Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Minato, A. Organometallics 1991, 10, 880. https://doi.org/10.1021/om00050a016
  12. Takaki, K.; Sakamoto, H.; Nishimura, Y.; Sugihara, Y.; Ishikawa, M. Organometallics 1991, 10, 888. https://doi.org/10.1021/om00050a017
  13. 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
  14. Ohshita, J.; Ohsaki, H.; Ishikawa, M. Organometallics 1991, 10, 2695. https://doi.org/10.1021/om00054a034
  15. Ishikawa, M.; Nishimura, Y.; Sakamoto, H. Organometallics 1991, 10, 2701. https://doi.org/10.1021/om00054a035
  16. 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
  17. Sakurai, H.; Sakamoto, K.; Kira, M. Chem. Lett. 1984, 1213.
  18. Kira, M.; Sakamoto, K.; Sakurai, H. J. Am. Chem. Soc. 1983, 105, 7469. https://doi.org/10.1021/ja00363a058
  19. Okinoshima, H.; Weber, W. P. J. Organomet. Chem. 1978, 149, 279. https://doi.org/10.1016/S0022-328X(00)90392-9
  20. Hu, S. S.; Weber, W. P. J. Organomet. Chem. 1989, 369, 155. https://doi.org/10.1016/0022-328X(89)88003-9
  21. Park, S. K. J. Photochem. Photobiol. A: Chem. 2005, 173, 29. https://doi.org/10.1016/j.jphotochem.2004.11.020
  22. Park, S. K. Bull. Korean Chem. Soc. 2006, 27, 1305. https://doi.org/10.5012/bkcs.2006.27.9.1305
  23. Park, S. K. Bull. Korean Chem. Soc. 2008, 29, 1018. https://doi.org/10.5012/bkcs.2008.29.5.1018
  24. Park, S. K.; Baek, D. J. J. Photochem. Photobiol. A: Chem. 2004, 163, 87 https://doi.org/10.1016/S1010-6030(03)00440-4
  25. Kira, M.; Miyazawa, T.; Sugiyama, H.; Yamaguchi, M.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 3116. https://doi.org/10.1021/ja00061a010
  26. Park, S. K. Bull. Korean Chem. Soc. 2007, 28, 1045. https://doi.org/10.5012/bkcs.2007.28.6.1045
  27. Lasorne, B.; Bearpark, M. J.; Robb, M. A.; Worth, G. A. J. Phys. Chem. A 2008, 112, 13017. https://doi.org/10.1021/jp803740a
  28. Bieri, G.; Heilbronner, E.; Kobayashi, T.; Schmelzer, A. Helvetica Chimica Acta 1976, 59, 2657. https://doi.org/10.1002/hlca.19760590805
  29. Harman, P. J.; Kent, J. E.; O'Dwyer, M. F.; Griffith, D. W. T. J. Phys. Chem. 1981, 85, 2731. https://doi.org/10.1021/j150619a008
  30. Franck, R. W.; Mandella, W. L.; Falci, K. J. J. Org. Chem. 1975, 40, 327. https://doi.org/10.1021/jo00891a013
  31. McDonald, R. N.; Reineke, C. E. J. Am. Chem. Soc. 1967, 32, 1878.
  32. Selms, R. C.; Schleigh, W. R. Tetrahedron Lett. 1972, 3563.
  33. Sato, M.; Katagiri, N.; Muto, M.; Haneda, T.; Kaneko, C. Tetrahedron Lett. 1986, 27, 6091. https://doi.org/10.1016/S0040-4039(00)85406-4
  34. Toda, F.; Tanaka, K. Tetrahedron Lett. 1988, 29, 4299. https://doi.org/10.1016/S0040-4039(00)80480-3
  35. Wu, L. C.; Cheer, C. J.; Olovsson, G.; Scheffer, J. R.; Trotter, J.; Wang, S. L.; Liao, F. L. Tetrahedron Lett. 1997, 38, 3135. https://doi.org/10.1016/S0040-4039(97)00615-1
  36. Bach, T.; Bergmann, H.; Harms, K. Organic Letters 2001, 3, 601. https://doi.org/10.1021/ol007004t

피인용 문헌

  1. ChemInform Abstract: A Novel Photoreaction of (2-Hydroxyethoxyphenyl)pentamethyldisilane. vol.40, pp.45, 2009, https://doi.org/10.1002/chin.200945171
  2. A Novel Photoreaction of (2-Propargyloxyphenyl)pentamethyldisilane vol.38, pp.6, 2017, https://doi.org/10.1002/bkcs.11132
  3. Photoinduced Rearrangement Reaction of 2-(Pentamethyldisilanyloxymethyl) phenylpentamethyldisilane vol.31, pp.3, 2009, https://doi.org/10.5012/bkcs.2010.31.03.731
  4. Photoreactions of (2-Acetoxyphenyl)pentamethyldisilane vol.32, pp.8, 2011, https://doi.org/10.5012/bkcs.2011.32.8.3155
  5. A Novel Photoreaction of (2-Hydroxypropoxyphenyl)pentamethyldisilane vol.33, pp.11, 2009, https://doi.org/10.5012/bkcs.2012.33.11.3823
  6. Direct Syn Addition of Two Silicon Atoms to a C≡C Triple Bond by Si−Si Bond Activation: Access to Reactive Disilylated Olefins vol.129, pp.9, 2009, https://doi.org/10.1002/ange.201611719
  7. Direct Syn Addition of Two Silicon Atoms to a C≡C Triple Bond by Si−Si Bond Activation: Access to Reactive Disilylated Olefins vol.56, pp.9, 2009, https://doi.org/10.1002/anie.201611719
  8. 2-브로모-3-(프로프-2-인-1-일옥시)피리딘과 1-클로로-1,1,2,2,2-펜타메칠디실란의 그리냐르 반응 vol.62, pp.4, 2009, https://doi.org/10.5012/jkcs.2018.62.4.314