A facile preparation and polymerization of 1,1-difunctionalized disiloxanes

Chemistry Letters

Volumn , Issue 7, 1996, Pages 517-518

  Mori, Atsunori ^a   Sato, Hiroyoshi ^a   Mizuno, Katsuya ^a   Hiyama, Tamejiro ^a   Shintani, Koji ^b   Kawakami, Yusuke ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030511638     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.517     Document Type: Article

References (20)

1. "The Analytical Chemistry of Silicones," ed by A. L. Smith, Wiley, New York (1991).
2. K. Ajima, M. Nomura, A. Mori, and Y. Kawakami, Polym. Prepr., Jpn., 44, 3011 (1995); Y. Kawakami, Y. Miki, T. Tsuda, R. A. N. Murthy, and Y. Yamashita, Polym. J., 14, 913 (1982); Y. Kawakami and T. Sugisaka, J. Memb. Sci., 50, 189 (1990); Y. Kawakami and K. Toida, Macromolecules, 28, 816 (1995) and references therein.
3. K. Ajima, M. Nomura, A. Mori, and Y. Kawakami, Polym. Prepr., Jpn., 44, 3011 (1995); Y. Kawakami, Y. Miki, T. Tsuda, R. A. N. Murthy, and Y. Yamashita, Polym. J., 14, 913 (1982); Y. Kawakami and T. Sugisaka, J. Memb. Sci., 50, 189 (1990); Y. Kawakami and K. Toida, Macromolecules, 28, 816 (1995) and references therein.
4. K. Ajima, M. Nomura, A. Mori, and Y. Kawakami, Polym. Prepr., Jpn., 44, 3011 (1995); Y. Kawakami, Y. Miki, T. Tsuda, R. A. N. Murthy, and Y. Yamashita, Polym. J., 14, 913 (1982); Y. Kawakami and T. Sugisaka, J. Memb. Sci., 50, 189 (1990); Y. Kawakami and K. Toida, Macromolecules, 28, 816 (1995) and references therein.
5. K. Ajima, M. Nomura, A. Mori, and Y. Kawakami, Polym. Prepr., Jpn., 44, 3011 (1995); Y. Kawakami, Y. Miki, T. Tsuda, R. A. N. Murthy, and Y. Yamashita, Polym. J., 14, 913 (1982); Y. Kawakami and T. Sugisaka, J. Memb. Sci., 50, 189 (1990); Y. Kawakami and K. Toida, Macromolecules, 28, 816 (1995) and references therein.
6. A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. See also: S. M. Sieburth and L. Fensterbank, J. Org. Chem., 58, 6314 (1993); S. M. Sieburth and W. Mu, J. Org. Chem, 58, 7854 (1993).
7. A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. See also: S. M. Sieburth and L. Fensterbank, J. Org. Chem., 58, 6314 (1993); S. M. Sieburth and W. Mu, J. Org. Chem, 58, 7854 (1993).
8. A. Mori, T. Hishida, Y. Soga, and Y. Kawakami, Chem. Lett., 1995, 107. See also: S. M. Sieburth and L. Fensterbank, J. Org. Chem., 58, 6314 (1993); S. M. Sieburth and W. Mu, J. Org. Chem, 58, 7854 (1993).
9. K. Shintani, Y. Soga, A. Mori, and Y. Kawakami, unpublished results.
10. Available from ShinEtsu Chemical Co. Ltd. The authors are grateful for kind donation of these reagents.
11. Four molar equivalents of alkyllithium were required to cleave the cyclic tetrasiloxane. The reaction was carried out at -30 °C to avoid undesireble side reaction.
12. -1.
13. Platinum(0) 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (0.05 mol%) was used as the catalyst: G. Chandra, P. Y. Lo, P. B. Hichcock, and M. F. Lappert, Organometallics, 6, 191 (1987).
14. M. Tsumura, T. Iwahara, and T. Hirose, Polym., J., 27, 1048 (1995); P. R. Dvornic and V. V. Gerov, Macromolecules, 27, 1068 (1994); P. R. Dovornic, V. V. Gerov, and M. N. Goverdarica, Macromolecules, 27, 7575 (1994).
15. M. Tsumura, T. Iwahara, and T. Hirose, Polym., J., 27, 1048 (1995); P. R. Dvornic and V. V. Gerov, Macromolecules, 27, 1068 (1994); P. R. Dovornic, V. V. Gerov, and M. N. Goverdarica, Macromolecules, 27, 7575 (1994).
16. M. Tsumura, T. Iwahara, and T. Hirose, Polym., J., 27, 1048 (1995); P. R. Dvornic and V. V. Gerov, Macromolecules, 27, 1068 (1994); P. R. Dovornic, V. V. Gerov, and M. N. Goverdarica, Macromolecules, 27, 7575 (1994).
17. 13C NMR.
18. Although the polymerization condition was not fully optimized, the reaction of 5 (hydrosilylation between siloxy olefin and siloxy silane) seems less reactive. Hydrosilylation polymerizations using monomers bearing olefin and hydrosilane: K. Shintani, Y. Soga, A. Mori, and Y. Kawakami, Abstract: The Society of Polymer Science, Japan, Hokuriku regional meeting A-23 (1995); Y. Pang, S. Ijadi-Maghsoodi, and T. J. Barton, Macromolecules, 26, 5671 (1993); T. Hayashi, S. Itsuno, K. Ito, and S. Yue, Polym. Prepr., Jpn., 44, 229 (1995).
19. Although the polymerization condition was not fully optimized, the reaction of 5 (hydrosilylation between siloxy olefin and siloxy silane) seems less reactive. Hydrosilylation polymerizations using monomers bearing olefin and hydrosilane: K. Shintani, Y. Soga, A. Mori, and Y. Kawakami, Abstract: The Society of Polymer Science, Japan, Hokuriku regional meeting A-23 (1995); Y. Pang, S. Ijadi-Maghsoodi, and T. J. Barton, Macromolecules, 26, 5671 (1993); T. Hayashi, S. Itsuno, K. Ito, and S. Yue, Polym. Prepr., Jpn., 44, 229 (1995).
20. Although the polymerization condition was not fully optimized, the reaction of 5 (hydrosilylation between siloxy olefin and siloxy silane) seems less reactive. Hydrosilylation polymerizations using monomers bearing olefin and hydrosilane: K. Shintani, Y. Soga, A. Mori, and Y. Kawakami, Abstract: The Society of Polymer Science, Japan, Hokuriku regional meeting A-23 (1995); Y. Pang, S. Ijadi-Maghsoodi, and T. J. Barton, Macromolecules, 26, 5671 (1993); T. Hayashi, S. Itsuno, K. Ito, and S. Yue, Polym. Prepr., Jpn., 44, 229 (1995).