Living polymerization of tert-butyl 4-vinylbenzoate by the SmI2/SmI3 system

Macromolecules

Volumn 31, Issue 10, 1998, Pages 3388-3390

  Gosho, Akiko ^a   Nomura, Ryoji ^b   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a Tokyo Institute of Technology ^*  (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000329909     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma971828h     Document Type: Article

References (25)

1. (a) Yasuda, H. Catalysis in Precision Polymerization; Kobayashi, S., Ed.; John Wiley & Sons: Chichester, England, 1997; Vol. 6, Chapter 4, p 189.
2. (b) Yasuda, H.; Ihara, E. Bull. Chem. Soc. Jpn. 1997, 70, 1745-1767.
3. 2 also failed to achieve the living polymerization of styrene. See: (c) Hu, J.; Shen, Q. Cuihua Xuebao 1993, 11, 16. And also ref 1.
4. 2 also failed to achieve the living polymerization of styrene. See: (c) Hu, J.; Shen, Q. Cuihua Xuebao 1993, 11, 16. And also ref 1.
5. 2 also failed to achieve the living polymerization of styrene. See: (c) Hu, J.; Shen, Q. Cuihua Xuebao 1993, 11, 16. And also ref 1.
6. The conventional living anionic polymerization of 1 was reported by Nakahama et al. See: (a) Nakahama, S.; Ishizone, T.; Hirao, A. Makromol. Chem., Macromol. Symp. 1993, 67, 223. (b) Ishizone, T.; Watabayashi, S.; Hirao, A.; Nakahama, S. Macromolecules 1989, 22, 2895.
7. The conventional living anionic polymerization of 1 was reported by Nakahama et al. See: (a) Nakahama, S.; Ishizone, T.; Hirao, A. Makromol. Chem., Macromol. Symp. 1993, 67, 223. (b) Ishizone, T.; Watabayashi, S.; Hirao, A.; Nakahama, S. Macromolecules 1989, 22, 2895.
8. 2 gave the corresponding dimerized product in 52% isolated yield. See ref 11.
9. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
10. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
11. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
12. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
13. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
14. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
15. For recent examples for the use of divalent samarium complexes as polymerization catalysts, see: (a) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134. (b) Evans, W. J.; Katsumata, H. Macromolecules 1994, 27, 4011. (c) Nakayama, Y.; Shibahara, T.; Fukumoti, H.; Nakamura, A.; Mashima, K. Macromolecules 1996, 29, 8014. (d) Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669. (e) Wang, J.; Nomura, R.; Endo, T. Macromolecules 1996, 29, 2707. (f) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (g) Boffa, L. S.; Novak, B. M. Tetrahedron 1997, 53, 15367.
16. 2 (2 mL, 0.2 mmol) and HMPA (0.2 mL, 1.2 mmol) was added 1 (1.49 mmol), and the solution was kept stirring at -40 °C for 24 h. After pouring into methanol, the precipitate was collected and dried in vacuo to give the polymer.
17. Nomura, R.; Endo, T. The Polymeric Materials Encyclopedia; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; Vol. 3, p 2016.
18. 3 in this polymerization. Further investigation to clarify the mechanism is ongoing.
19. 3 in this polymerization. Further investigation to clarify the mechanism is ongoing.
20. 3 in this polymerization. Further investigation to clarify the mechanism is ongoing.
21. 3 in this polymerization. Further investigation to clarify the mechanism is ongoing.
22. 3 in this polymerization. Further investigation to clarify the mechanism is ongoing.
23. 1H NMR analysis indicated that the stereoregularity of the obtained polymer was atactic.
24. 3 gave no polymer, and the monomer was recovered, although smooth oxidation of Sm(II) into Sm(III) was confirmed by the color change of the solution.
25. Gosho, A.; Nomura, R.; Endo, T. Jpn. J. Polym. Sci. Technol. 1997, 54, 886.