Substituent effects on catalytic synthesis and properties of poly(phenylsilane)

Chemistry Letters

Volumn , Issue 2, 2000, Pages 188-189

  Hashimoto, Hisako ^a   Obara, Sachiko ^a   Kira, Mitsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034336083     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.188     Document Type: Article

References (26)

1. For reviews, see; R. West, J. Organomet. Chem., 300, 327 (1986); R. West, in "The Chemistry of Organosilicon Compounds," ed by S. Patai, Z. Rappoport, John Wiley and Sons, New York (1989), Chap. 19, p. 1207; D. R. Miller and J. Michl, Chem. Rev., 89, 1359 (1989); J. M. Siege and F. W. G. Fearons in "Silicon-Based Polymer Science: A Comprehensive Resource, Advances in Chemistry Series," American Chemical Society, Washington, D. C. (1990), Vol. 224.
2. For reviews, see; R. West, J. Organomet. Chem., 300, 327 (1986); R. West, in "The Chemistry of Organosilicon Compounds," ed by S. Patai, Z. Rappoport, John Wiley and Sons, New York (1989), Chap. 19, p. 1207; D. R. Miller and J. Michl, Chem. Rev., 89, 1359 (1989); J. M. Siege and F. W. G. Fearons in "Silicon-Based Polymer Science: A Comprehensive Resource, Advances in Chemistry Series," American Chemical Society, Washington, D. C. (1990), Vol. 224.
3. For reviews, see; R. West, J. Organomet. Chem., 300, 327 (1986); R. West, in "The Chemistry of Organosilicon Compounds," ed by S. Patai, Z. Rappoport, John Wiley and Sons, New York (1989), Chap. 19, p. 1207; D. R. Miller and J. Michl, Chem. Rev., 89, 1359 (1989); J. M. Siege and F. W. G. Fearons in "Silicon-Based Polymer Science: A Comprehensive Resource, Advances in Chemistry Series," American Chemical Society, Washington, D. C. (1990), Vol. 224.
4. For reviews, see; R. West, J. Organomet. Chem., 300, 327 (1986); R. West, in "The Chemistry of Organosilicon Compounds," ed by S. Patai, Z. Rappoport, John Wiley and Sons, New York (1989), Chap. 19, p. 1207; D. R. Miller and J. Michl, Chem. Rev., 89, 1359 (1989); J. M. Siege and F. W. G. Fearons in "Silicon-Based Polymer Science: A Comprehensive Resource, Advances in Chemistry Series," American Chemical Society, Washington, D. C. (1990), Vol. 224.
5. Several polysilanes having a trifluoromethyl or an alkoxy group at the terminal of the side chains were synthesized by the Wurtz-coupling. Inter alia: M. Fujino, T. Hisaki, M. Fujiki, and N. Matsumoto, Macromolecules, 25, 1079 (1992); C. - H. Yuan, R. West, Macromolecules, 26, 2645 (1993); H. Frey, G. J. J. Out, M. Möller, D. Greszta, and K. Matyjaszewski, Macromolecules, 26, 6231 (1993); Y. Nakano, S. Murai, R. Kani, and S. Hayase, J. Polym. Sci., Part A; Polym. Chem., 31 3361 (1993).
6. Several polysilanes having a trifluoromethyl or an alkoxy group at the terminal of the side chains were synthesized by the Wurtz-coupling. Inter alia: M. Fujino, T. Hisaki, M. Fujiki, and N. Matsumoto, Macromolecules, 25, 1079 (1992); C. - H. Yuan, R. West, Macromolecules, 26, 2645 (1993); H. Frey, G. J. J. Out, M. Möller, D. Greszta, and K. Matyjaszewski, Macromolecules, 26, 6231 (1993); Y. Nakano, S. Murai, R. Kani, and S. Hayase, J. Polym. Sci., Part A; Polym. Chem., 31 3361 (1993).
7. Several polysilanes having a trifluoromethyl or an alkoxy group at the terminal of the side chains were synthesized by the Wurtz-coupling. Inter alia: M. Fujino, T. Hisaki, M. Fujiki, and N. Matsumoto, Macromolecules, 25, 1079 (1992); C. - H. Yuan, R. West, Macromolecules, 26, 2645 (1993); H. Frey, G. J. J. Out, M. Möller, D. Greszta, and K. Matyjaszewski, Macromolecules, 26, 6231 (1993); Y. Nakano, S. Murai, R. Kani, and S. Hayase, J. Polym. Sci., Part A; Polym. Chem., 31 3361 (1993).
8. Several polysilanes having a trifluoromethyl or an alkoxy group at the terminal of the side chains were synthesized by the Wurtz-coupling. Inter alia: M. Fujino, T. Hisaki, M. Fujiki, and N. Matsumoto, Macromolecules, 25, 1079 (1992); C. - H. Yuan, R. West, Macromolecules, 26, 2645 (1993); H. Frey, G. J. J. Out, M. Möller, D. Greszta, and K. Matyjaszewski, Macromolecules, 26, 6231 (1993); Y. Nakano, S. Murai, R. Kani, and S. Hayase, J. Polym. Sci., Part A; Polym. Chem., 31 3361 (1993).
9. For multi-step functionalization of polysilanes, see: a) W. Uhlig, J. Organomet. Chem., 402, C45 (1991).
10. b) U. Herzog and R. West, Macromolecules, 32, 2210 (1999).
11. c) J. P. Banovetz, Y.-L. Hsiao and R. M. Waymouth, J. Am. Chem. Soc., 115, 2540 (1993).
12. d) Y.-L. Hsiao and R. M. Waymouth, J. Am. Chem. Soc., 116, 9779 (1994).
13. For recent reviews, see; F. Bauvin, J. F. Harrod, and H-. G. Woo, Adv. Organomet. Chem., 42, 363 (1998); J. Y. Corey, J. L. Huhmann, R. M. Shaltout, and D. M. Kraichely, in "Progress in Organosilicon Chemistry," ed by B. Marciniec and J. Chojnowski, Gordon and Breach Publishers, Australia (1995), p. 387; T. D. Tilley, Acc. Chem. Res., 26, 22 (1993).
14. For recent reviews, see; F. Bauvin, J. F. Harrod, and H-. G. Woo, Adv. Organomet. Chem., 42, 363 (1998); J. Y. Corey, J. L. Huhmann, R. M. Shaltout, and D. M. Kraichely, in "Progress in Organosilicon Chemistry," ed by B. Marciniec and J. Chojnowski, Gordon and Breach Publishers, Australia (1995), p. 387; T. D. Tilley, Acc. Chem. Res., 26, 22 (1993).
15. For recent reviews, see; F. Bauvin, J. F. Harrod, and H-. G. Woo, Adv. Organomet. Chem., 42, 363 (1998); J. Y. Corey, J. L. Huhmann, R. M. Shaltout, and D. M. Kraichely, in "Progress in Organosilicon Chemistry," ed by B. Marciniec and J. Chojnowski, Gordon and Breach Publishers, Australia (1995), p. 387; T. D. Tilley, Acc. Chem. Res., 26, 22 (1993).
16. 8, δ) -64 ∼ -60. The structure of the polymers obtained from (pentafluoro)-phenylsilane and m,m'-bis(trifluoromethyl)phenylsilane was not determined because of their low solubility in the solvents. These two polymers may not be the linear polysilanes.
17. Y. Obora and M. Tanaka, 45th Symposium on Organometallic Chemistry, Japan, Tokyo, September, 1998, Abstr., No. PA116.
18. 4
19. V. K. Dioumaev and J. F. Harrod, Organometallics, 13, 1548 (1994).
20. J. P. Banovetz, H. Suzuki, and R. M. Waymouth, Organometallics, 12, 4700 (1993).
21. Since the NMR signals of our polysilanes are rather broad, we assigned them as atactic structures, although there is a controversy on stereochemistry of poly(phenylsilane) obtained by dehydrogenative coupling. J. P. Banovetz, K. M. Stain, and R. M. Waymouth, Organometallics, 10, 3430 (1991); N. Choi, S.-Y. Onozawa, T. Sakakura, and M. Tanaka, Organometallics, 16, 2765 (1997); B. J. Grimmond and J. Y. Corey, Organometallics, 18, 2223 (1999); V. K. Dioumaev, K. Rahimian, F. Gauvin, and J. F. Harrod, Organometallics, 18, 2249 (1999).
22. Since the NMR signals of our polysilanes are rather broad, we assigned them as atactic structures, although there is a controversy on stereochemistry of poly(phenylsilane) obtained by dehydrogenative coupling. J. P. Banovetz, K. M. Stain, and R. M. Waymouth, Organometallics, 10, 3430 (1991); N. Choi, S.-Y. Onozawa, T. Sakakura, and M. Tanaka, Organometallics, 16, 2765 (1997); B. J. Grimmond and J. Y. Corey, Organometallics, 18, 2223 (1999); V. K. Dioumaev, K. Rahimian, F. Gauvin, and J. F. Harrod, Organometallics, 18, 2249 (1999).
23. Since the NMR signals of our polysilanes are rather broad, we assigned them as atactic structures, although there is a controversy on stereochemistry of poly(phenylsilane) obtained by dehydrogenative coupling. J. P. Banovetz, K. M. Stain, and R. M. Waymouth, Organometallics, 10, 3430 (1991); N. Choi, S.-Y. Onozawa, T. Sakakura, and M. Tanaka, Organometallics, 16, 2765 (1997); B. J. Grimmond and J. Y. Corey, Organometallics, 18, 2223 (1999); V. K. Dioumaev, K. Rahimian, F. Gauvin, and J. F. Harrod, Organometallics, 18, 2249 (1999).
24. Since the NMR signals of our polysilanes are rather broad, we assigned them as atactic structures, although there is a controversy on stereochemistry of poly(phenylsilane) obtained by dehydrogenative coupling. J. P. Banovetz, K. M. Stain, and R. M. Waymouth, Organometallics, 10, 3430 (1991); N. Choi, S.-Y. Onozawa, T. Sakakura, and M. Tanaka, Organometallics, 16, 2765 (1997); B. J. Grimmond and J. Y. Corey, Organometallics, 18, 2223 (1999); V. K. Dioumaev, K. Rahimian, F. Gauvin, and J. F. Harrod, Organometallics, 18, 2249 (1999).
25. R. D. Miller and R. Sooriyakumaran, J. Polym. Sci., Polym. Lett. Ed., 21, 823 (1983).
26. 4-substituted polysilanes.