The effect of the N-substituent s-trans to the carbonyl group of N-methylacrylamide derivatives on the stereospecificity of radical polymerizations

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 47, Issue 23, 2009, Pages 6534-6539

  Hirano, Tomohiro ^a   Nasu, Shou ^a   Morikami, Akihiro ^a   Ute, Koichi ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Isotactic; Monomer conformation; N methyl N phenylacrylamide; Radical polymerization; Stereospecific polymerization; Syndiotactic

Indexed keywords

ISOTACTIC; ISOTACTICS; RADICAL POLYMERIZATION; STEREOSPECIFIC POLYMERIZATIONS; SYNDIOTACTICS;

AMIDES; ATOM TRANSFER RADICAL POLYMERIZATION; CONFORMATIONS; FLUORINE CONTAINING POLYMERS; FREE RADICAL POLYMERIZATION; MONOMERS; POLYMERS; TOLUENE;

ACRYLIC MONOMERS;

EID: 72449160116     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23696     Document Type: Article

References (52)

1. (a) Yuki, H.; Hatada, K.; Niinomi, Y.; Kikuchi, Y. Polym J 1970, 1, 36-45
2. (b) Nakano, T.; Matsuda, A.; Okamoto, Y. Polym J 1996, 28, 556-558;
3. (c) Nakano, T.; Shikisai, Y.; Okamoto, Y. Polym J 1996, 28, 51-60.
4. (a) Hoshikawa, N.; Hotta, Y.; Okamoto, Y. J Am Chem Soc 2003, 125, 12380-12381
5. (b) Azam, A. K. M. F.; Kamigaito, M.; Okamoto, Y. Polym J 2006, 38, 1035-1042
6. (c) Azam, A. K. M. F.; Kamigaito, M.; Okamoto, Y. J Polym Sci Part A: Polym Chem 2007, 45, 1304-1315.
7. (a) Porter, N. A.; Allen, T. R.; Breyer R. A. J Am Chem Soc 1992, 114, 7676-7683
8. (b) Wu, W.-X.; McPhail, A. T.; Porter, N. A. J Org Chem 1994, 59, 1302-1308.
9. (b) Liu, W.; Nakano, T.; Okamoto, Y. Polym J 2000, 32, 771-777.
10. (b) Kaneko, Y.; Iwakiri, N.; Sato, S.; Kadokawa, J. Macromolecules 2008, 41, 489-492.
11. (a) Hirano, T.; Tateiwa, S.; Seno, M.; Sato, T. J Polym Sci Part A: Polym Chem 2000, 38, 2487-2491
12. (b) Hirano, T.; Takeyoshi, R.; Seno, M.; Sato, T. J Polym Sci Part A: Polym Chem 2002, 40, 2425-2426.
13. (a) Isobe, Y.; Fujioka, D.; Habaue, S.; Okamoto, Y. J Am Chem Soc 2001, 123, 7180-7181
14. (b) Habaue, S.; Isobe, Y.; Okamoto, Y. Tetrahedron 2002, 58, 8205-8209.
15. (a) Habaue, S.; Baraki, H.; Okamoto, Y. Polym J 2000, 32, 1017-1021
16. (b) Habaue, S.; Uno, T.; Baraki, H.; Okamoto, Y. Macromolecules 2000, 33, 820-824
17. (c) Baraki, H.; Habaue, S.; Okamoto, Y. Macromolecules 2001, 34, 4724-4729.
18. Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605.
19. (a) Isobe, Y.; Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1999, 32, 5979-5981
20. (b) Isobe, Y.; Yamada, K.; Nakano, T.; Okamoto, Y. J Polym Sci Part A: Polym Chem 2000, 38, 4693-4703.
21. (a) Hirano, T.; Miki, H.; Seno, M.; Sato, T. Polymer 2005, 46, 3693-3699
22. (b) Hirano, T.; Ishii, S.; Kitajima, H.; Seno, M.; Sato, T. J Polym Sci Part A: Polym Chem 2005, 43, 50-62
23. (c) Hirano, T.; Kitajima, H.; Seno, M.; Sato T. Polymer 2006, 47, 539-546.
24. (a) Hirano, T.; Ishizu, H.; Seno, M.; Sato, T. Polymer 2005, 46, 10607-10610
25. (b) Hirano, T.; Ishizu, M.; Sato, T. Polymer 2008, 49, 438-445;
26. (c) Hirano, T.; Ishizu, M.; Yamaoka, R.; Ute, K. Sato T. Polymer 2009, 50, 3522-3527.
27. (a) Hirano, T.; Okumura, Y.; Kitajima, H.; Seno, M.; Sato, T. J Polym Sci Part A: Polym Chem 2006, 44, 4450-4460
28. (b) Hirano, T.; Kamikubo, T.; Fujioka, Y.; Sato, T. Eur Polym J 2008, 44, 1053-1059.
29. (a) Hirano, T.; Kamikubo, T.; Okumura, Y.; Sato, T. Polymer 2007, 48, 4921-4925;
30. (b) Hirano, T.; Kamikubo, T.; Okumura, Y.; Bando, Y.; Yamaoka, R.; Mori, T.; Ute, K. J Polym Sci Part A: Polym Chem 2009, 47, 2539-2550.
31. Hirano, T.; Nakamura, K.; Kamikubo, T.; Ishii, S.; Tani, K.; Mori, T.; Sato, T. J Polym Sci Part A: Polym Chem 2008, 46, 4575-4583.
32. Hirano, T.; Miyazaki, T.; Ute, K. J Polym Sci Part A: Polym Chem 2008, 46, 5698-5701.
33. Wan, D.; Satoh, K.; Kamigaito, M. Macromolecules 2006, 39, 6882-6886.
34. (a) Hirano, T.; Masuda, S.; Sato, T. J Polym Sci Part A: Polym Chem 2008, 46, 3145-3149
35. (b) Hirano, T.; Masuda, S.; Nasu, S.; Ute, K.; Sato, T. J Polym Sci Part A: Polym Chem 2009, 47, 1192-1203.
36. Wan, D.; Satoh, K.; Kamigaito, M.; Okamoto, Y. Macromolecules 2005, 38, 10397-10405.
37. Hirano, T.; Okumura, Y.; Seno, M.; Sato, T. Eur Polym J 2006, 42, 2114-2124.
38. Ajiro, H.; Akashi, M. Macromolecules 2009, 42, 489-493.
39. (a)Serizawa, T.; Hamada, K.; Akashi, M. Nature 2004, 429, 52-55
40. (b) Serizawa, T.; Akashi, M. Polym J 2006, 38, 311-328.
41. Uemura, T.; Ono, Y.; Kitagawa, K.; Kitagawa, S. Macromolecules 2008, 41, 87-94.
42. (a) Matsumoto, A. Polym J 2003, 35, 93-121
43. (b) Nagahama, S.; Tanaka, T.; Matsumoto, A. Angew Chem Int Ed Engl 2004, 43, 3811-3814.
44. Yamasaki, R.; Tanatani, A.; Azumaya, I.; Saito, S.; Yamaguchi, K.; Kagechika, H. Org Lett 2003, 5, 1265-1267.
45. Zhang, Z.; Chung, T. C. M. Macromolecules 2006, 39, 5187-5189.
46. Wójcik, J.; Witanowski, M.; Stefaniak, L. Bull Acad Pol Sci Ser Sci Chim 1978, 26, 927-932.
47. (a) Pedersen, B. F. Acta Chem Scand 1967, 21, 1415-1424
48. (b) Itai, A.; Toriumi, Y.; Tomioka, N.; Kagechika, H.; Azumaya, I.; Shudo, K. Tetrahedron Lett 1989, 30, 6177-6180
49. (c) Yamaguchi, K.; Matsumura, G.; Kagechika, H.; Azumaya, I.; Ito, Y.; Itai, A.; Shudo, K. J Am Chem Soc 1991, 113, 5474-5475
50. (d) Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J Am Chem Soc 1992, 114, 10649-10659
51. (e) Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J Org Chem 1995, 60, 4715-4720.
52. Fordham, J. W. L. J Polym Sci 1959, 39, 321-334