A ruthenium-catalyzed hydrosilane-induced polymerization of 3-alkyl-3-hydroxymethyloxetane derivatives: Facile access to functionalized polyoxetanes by virtue of organosilyl groups

Bulletin of the Chemical Society of Japan

Volumn 84, Issue 1, 2011, Pages 26-39

  Harada, Nari Aki ^a   Yasuhara, Jushiro ^a   Motoyama, Yukihiro ^a   Fujimura, Osamu ^b   Tsuji, Tetsuro ^b   Takahashi, Takeshi ^b   Takahashi, Yoshiaki ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b UBE INDUSTRIES LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYZED REACTIONS; CONSUMPTION RATES; FACILE ACCESS; FUNCTIONALIZED; HYDROSILANES; ONE-POT SYNTHESIS; OXETANES; POLYMER PROPERTIES; POLYOXETANES; RANDOM COPOLYMER; SIDE CHAINS; SILYLATIONS; TRIALKYLSILANES;

ALKYLATION; CATALYSIS; COPOLYMERIZATION; COPOLYMERS; FUNCTIONAL GROUPS; POLYMERS; RING OPENING POLYMERIZATION; RUTHENIUM; SYNTHESIS (CHEMICAL);

FUNCTIONAL POLYMERS;

EID: 78751475671     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20100155     Document Type: Article

References (50)

1. A. J. Chalk, J. Chem. Soc. D 1970, 847.
2. J.V.Crivello, M. Fan, J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 1.
3. J. V. Crivello, M. Fan, J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1853.
4. J. V. Crivello, M. Fan, J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 31.
5. H. Nagashima, A. Suzuki, T. Iura, K. Ryu, K. Matsubara, Organometallics 2000, 19, 3579.
6. H. Nagashima, C. Itonaga, J. Yasuhara, Y. Motoyama, K. Matsubara, Organometallics 2004, 23, 5779.
7. D. B. Pattison, J. Am. Chem. Soc. 1957, 79, 3455.
8. U. Annby, N. Rehnberg, J. Samuelsson, O. Teichert, Org. Process Res. Dev. 2001, 5, 568.
9. M. Bednarek, T. Biedron, J. Heilinski, K. Kaluzynski, P. Kubisa, S. Penczek, Macromol. Rapid Commun. 1999, 20, 369.
10. P. Kubisa, S. Penczek, Prog. Polym. Sci. 1999, 24, 1409.
11. D. Yan, J. Hou, X. Zhu, J. J. Kosman, H.-S. Wu, Macromol. Rapid Commun. 2000, 21, 557.
12. M. Bednarek, P. Kubisa, S. Penczek, Macromolecules 2001, 34, 5112.
13. J. Hou, D. Yan, Macromol. Rapid Commun. 2002, 23, 456.
14. J. Xu, Y.-F. Zou, C.-Y. Pan, J. Macromol. Sci., Part A: Pure Appl. Chem. 2002, 39, 431.
15. Y. Mai, Y. Zhou, D. Yan, H. Lu, Macromolecules 2003, 36, 9667.
16. M. Bednarek, Polym. Int. 2003, 52, 1595.
17. P. Kubisa, J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 457.
18. Q. Zhu, J. Wu, C. Tu, Y. Shi, L. He, R. Wang, X. Zhu, D. Yan, J. Phys. Chem. B 2009, 113, 5777.
19. M. Rahm, R. Westlund, C. Eldsäter, E. Malmström, J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 6191.
20. Q. Tan, L. Wang, L. Ma, H. Yu, Q. Liu, A. Xiao, Macromolecules 2009, 42, 4500.
21. M. Bednarek, M. Pluta, Macromol. Symp. 2010, 287, 119.
22. H. Cheng, S. Xie, Y. Zhou, W. Huang, D. Yan, J. Yang, B. Ji, J. Phys. Chem. B 2010, 114, 6291.
23. H. Cheng, X. Yuan, X. Sun, K. Li, Y. Zhou, D. Yan, Macromolecules 2010, 43, 1143.
24. M. Motoi, H. Suda, K. Shimamura, S. Nagahara, M. Takei, S. Kanoh, Bull. Chem. Soc. Jpn. 1988, 61, 1653.
25. E. J. Vandenberg, J. C. Mullis, R. S. Juvet, Jr., J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 3083.
26. Y. Kawakami, K. Takahashi, S. Nishiguchi, K. Toida, Polym. Int. 1993, 31, 35.
27. M. Motoi, K. Noguchi, A. Arano, S. Kanoh, A. Ueyama, Bull. Chem. Soc. Jpn. 1993, 66, 1778.
28. B. Ameduri, B. Boutevin, L. Karam, J. Fluorine Chem. 1993, 65, 43.
29. H. Ogawa, T. Hosomi, T. Kosaka, S. Kanoh, A. Ueyama, M. Motoi, Bull. Chem. Soc. Jpn. 1997, 70, 175.
30. Y.-H. Xu, T. Yoshida, S. Kanoh, M. Motoi, React. Funct. Polym. 1998, 37, 65.
31. T. Sato, T. Oki, M. Seno, T. Hirano, J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1269.
32. T. Fujiwara, U. Makal, K. J. Wynne, Macromolecules 2003, 36, 9383.
33. L. Ye, Z. Feng, Y. Su, F. Wu, S. Chen, G. Wang, Polym. Int. 2005, 54, 1440.
34. U. Makal, J. Uilk, P. Kurt, R. S. Cooke, K. J. Wynne, Polymer 2005, 46, 2522.
35. C. Wesdemiotis, F. Pingitore, M. J. Polce, V. M. Russell, Y. Kim, C. M. Kausch, T. H. Connors, R. E. Medsker, R. R. Thomas, Macromolecules 2006, 39, 8369.
36. P. Kurt, K. J. Wynne, Macromolecules 2007, 40, 9537.
37. L. Ye, Y. Zhao, Z. Feng, Y. Bai, F. Wu, Front. Chem. Eng. China 2007, 1, 343.
38. A. Ertekin, Y. Kim, C. M. Kausch, R. R. Thomas, J. Colloid Interface Sci. 2009, 336, 40.
39. n
40. 2 moiety was seen in the hyperbranched polymer. Similarly, the integral ratio of the signal due to methylene protons of the ethyl group vs. CH2 groups in the polymer chain are also good proof; an ideal ratio is 1:2 in the linear polymer, whereas that is 1:3 in the hyperbranched polymer. This clearly showed that hyperbranched structure was not included in poly(EHO-SiMe2Ph) formed from of EHO-H by the ruthenium-catalyzed dehydrogenative silylation and subsequent ring-opening polymerization.
41. 2-, were separated by oxygen atoms; this reduce the magnetic interaction.
42. K. Tamao, T. Yamauchi, Y. Ito, Chem. Lett. 1987, 171.
43. A. G. Shipov, E. P. Kramarova, E. A. Mamaeva, O. A. Zamyshlyaeva, V. V. Negrebetsky, Y. E. Ovchinnikov, S. A. Pogozhikh, A. R. Bassindale, P. G. Taylor, Y. I. Baukov, J. Organomet. Chem. 2001, 620, 139.
44. S. D. Stamatov, J. Stawinski, Eur. J. Org. Chem. 2008, 2635.
45. E. Pérez, M. A. Gómez, A. Bello, J. G. Fatou, Polym. Sci. 1983, 261, 571.
46. E. Pérez, A. Bello, J. M. Pereña, Polym. Bull. 1988, 20, 291.
47. A. Bello, E. Perez, Thermochim. Acta 1988, 134, 155.
48. T. G. Fox, Bull. Am. Phys. Soc. 1956, 1, 123.
49. Polymers obtained by the present method are brownish solids due to the ruthenium residues, which are not completely removable by precipitation. Further treatment of the polymers with activated carbon or activated clay makes them colorless.
50. Y. Motoyama, C. Itonaga, T. Ishida, M. Takasaki, H. Nagashima, Org. Synth. 2005, 82, 188.