Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.5.1018

Photoreactions of 2-(Pentamethyldisilanyloxy)phenylpentamethyldisilane  

Park, Seung-Ki (Department of Chemistry, College of Natural Sciences, The University of Suwon)
Publication Information
Abstract
Photolysis of 2-(pentamethyldisilanyloxy)phenylpentamethyldisilane 1 in methanol provides five photoproducts 3, 4, 5, 6, and 7. Compounds 3 and 4 were probably formed from the methanol addition reactions of silene intermediate 2 and the formation of 5, 6, and 7 can best be explained by the nucleophilic attack of methanol to silicon atom in pentamethyldisilanyloxy or pentamethyldisilanyl group of the photoexcited state of 1. Irradiation of 1 in n-hexane gives a photoproduct 6 via silyl radical intermediate 8 and a novel intramolecular cyclization photoproduct 11 via silene 9 and silyl radical intermediate 10. Irradiation of 1 in deaerated methylene chloride in the presence of acetone affords a novel photoproduct 11 and phenol 7 but the expected photoproducts from the reaction of the silene intermediate with acetone were not obtained.
Keywords
2-(Pentamethyldisilanyloxy)phenylpentamethyldisilane; Silene
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Ishikawa, M.; Kikuchi, M.; Watanabe, K.; Sakamoto, H.; Kunai, A. J. Organomet. Chem. 1993, 443, C3   DOI   ScienceOn
2 Leigh, W. J.; Sluggett, G. W. J. Am. Chem. Soc. 1994, 116, 10468   DOI   ScienceOn
3 Steinmetz, M. G. Chem. Rev. 1995, 95, 1527   DOI   ScienceOn
4 Sakurai, H.; Nakadaira, Y.; Kira, M.; Sugiyama, H.; Yoshida, K.; Takiguchi, T. J. Organomet. Chem. 1980, 184, C36   DOI   ScienceOn
5 Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1977, 127, 261   DOI   ScienceOn
6 Ohshita, J.; Niwa, H.; Ishikawa, M. Organometallics 1996, 15, 4632   DOI   ScienceOn
7 Toltl, N. P.; Leigh, W. J. Organometallics 1996, 15, 2554   DOI   ScienceOn
8 Leigh, W. J.; Sluggett, G. W. Organometallics 1994, 13, 269   DOI   ScienceOn
9 Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1976, 118, 139   DOI   ScienceOn
10 Ishikawa, M. Pure Appl. Chem. 1978, 50, 11   DOI
11 Barton, T. J. Pure Appl. Chem. 1980, 52, 615   DOI
12 Nate, K.; Ishikawa, M.; Ni, H.; Watanabe, H.; Saheki, Y. Organometallics 1987, 6, 1673   DOI
13 Takaki, K.; Sakamoto, H.; Nishimura, Y.; Sugihara, Y.; Ishikawa, M. Organometallics 1991, 10, 888   DOI
14 Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Tsukihara, T.; Takahashi, K.; Kiso, Y. Organometallics 1991, 10, 2685   DOI
15 Ishikawa, M.; Nishimura, Y.; Sakamoto, H. Organometallics 1991, 10, 2701   DOI
16 Brook, A. G. In The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; pp 965-1005
17 Wiberg, N. J. Organomet. Chem. 1984, 273, 141   DOI   ScienceOn
18 Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419   DOI
19 Brook, A. G.; Baines, K. M. Adv. Organomet. Chem. 1986, 25, 1   DOI
20 Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; pp 1044-1102
21 Ishikawa, M.; Sakamoto, H.; Kanetani, F.; Minato, A. Organometallics 1989, 8, 2767   DOI
22 Ohshita, J.; Ohsaki, H.; Ishikawa, M.; Tachibana, A.; Kurosaki, Y.; Yamabe, T.; Minato, A. Organometallics 1991, 10, 880   DOI
23 Park, S. K. Bull. Korean Chem. Soc. 2007, 28, 1045   DOI   ScienceOn
24 Park, S. K. J. Photochem. Photobiol. A: Chem. 2005, 173, 29   DOI   ScienceOn
25 Park, S. K. Bull. Korean Chem. Soc. 2006, 27, 1305   DOI   ScienceOn
26 Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1978, 162, 223   DOI   ScienceOn
27 Sakurai, H. J. Organomet. Chem. 1980, 200, 261   DOI   ScienceOn
28 Guselnikov, L. E.; Nametkin, N. S. Chem. Rev. 1979, 79, 529   DOI
29 Kira, M.; Miyazawa, T.; Sugiyama, H.; Yamaguchi, M.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 3116   DOI   ScienceOn
30 Ishikawa, M.; Fuchikami, T.; Sugaya, T.; Kumada, M. J. Am. Chem. Soc. 1975, 97, 5923   DOI
31 Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1976, 118, 155   DOI   ScienceOn
32 Ohshita, J.; Ohsaki, H.; Ishikawa, M. Organometallics 1991, 10, 2695   DOI
33 Ohshita, J.; Niwa, H.; Ishikawa, M.; Yamabe, T.; Yoshii, T.; Nakamura, K. J. Am. Chem. Soc. 1996, 118, 6853   DOI   ScienceOn
34 Ishikawa, M.; Oda, M.; Miyoshi, N.; Fabry, L.; Kumada, M.; Yamabe, T.; Akagi, K.; Fukui, K. J. Am. Chem. Soc. 1979, 101, 4612   DOI
35 Morkin, T. L.; Leigh, W. J. Acc. Chem. Res. 2001, 34, 129   DOI   ScienceOn
36 Ishikawa, M.; Fuchikami, T.; Kumada, M. J. Organomet. Chem. 1977, 133, 19   DOI   ScienceOn
37 Ishikawa, M.; Kikuchi, M.; Kunai, A.; Takeuchi, T.; Tsukihara, T.; Kido, M. Organometallics 1993, 12, 3474   DOI   ScienceOn