Thiourea-mediated stereospecific radical polymerization of acrylamides and combination with RAFT for simultaneous control of molecular weight and tacticity

ACS Symposium Series

Volumn 1024, Issue , 2009, Pages 49-63

  Murayama, Harumi ^a   Satoh, Kotaro ^a   Kamigaito, Masami ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC MONOMERS; ATOM TRANSFER RADICAL POLYMERIZATION; DIMERS; HYDROGEN BONDS; LIVING POLYMERIZATION; MOLECULAR WEIGHT; POLYMERS; THIOUREAS;

CONTROLLED MOLECULAR WEIGHT; HYDROGEN BONDING INTERACTIONS; LIVING RADICAL POLYMERIZATION; N ,N-DIMETHYLACRYLAMIDE; N-ISOPROPYLACRYLAMIDES; PHENYL SUBSTITUENTS; SIMULTANEOUS CONTROL; THIOUREA DERIVATIVES;

FREE RADICAL POLYMERIZATION;

EID: 73249135492     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2009-1024.ch004     Document Type: Conference Paper

References (57)

1. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987-2988.
2. Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185-11186.
3. Wayland, B. B.; Poszmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943-7944.
4. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721-1723.
5. Wang, J.-S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615.
6. Percec, V.; Barboiu, B. Macromolecules 1995, 28, 7970-7972.
7. Granel, C.; Dubois, P.; Jérôme, R.; Teyssié, P. Macromolecules 1996, 29, 8576-8582.
8. Haddleton, D. M.; Jasieczek, C. B.; Hannon, M. J.; Shooter, A. J. Macromolecules 1997, 30, 2190-2193.
9. Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J. Jeffery, K.; Tam, P. T. Le.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559-5562.
10. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
11. Studer, A.; Schulte, T. Chem. Rec. 2005, 5, 27-35.
12. (a) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3745.
13. (b) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rec. 2004, 4, 159-175.
14. (c) Ouchi, M.; Terashima, T.; Sawamoto, M. Acc. Chem. Res. 2008, 41, 1120-1132.
15. (a) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
16. (b) Tsarevsky, N. V.; Matyjaszewski, K. Chem. Rev. 2007, 107, 2270-2299.
17. (c) Braunecker, W. A.; Matyjaszewski, K. Prog. Polym. Sci. 2007, 32, 93-146.
18. (a) Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2005, 58, 379-410.
19. (b) Moad, G.; Rizzardo, E.; Thang, S. H. Polymer 2008, 49, 1079-1131.
20. (c) Moad, G.; Rizzardo, E.; Thang, S. H. Acc. Chem. Res. 2008, 41, 1133-1142.
21. David, G.; Boyer, C.; Tonnar, J.; Ameduri, B.; Lacroix-Desmazes, P.; Boutevin, B. Chem. Rev. 2006, 106, 3936-3962.
22. Yamago, S. J. Polym. Sci.: Part A: Polym. Chem. 2006, 44, 1-12.
23. Poli, R.; Angew. Chem. Int. Ed. 2006, 45, 5058-5070.
24. (a) Yamada, K.; Nakano, T.; Okamoto, Y. Macromolecules 1998, 31, 7598-7605.
25. (b) Isobe, Y.; Yamada, K.; Nakano, T. Okamoto, Y. Macromolecules 1999, 32, 5979-5981.
26. Matsumoto, A.; Nakamura, S. J. Appl. Polym. Sci. 1999, 74, 290-296.
27. (a) Suito, Y.; Isobe, Y.; Habaue, S.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2496-2500.
28. (b) Isobe, Y.; Fujioka, D.; Habaue, S.; Okamoto, Y. J. Am. Chem. Soc. 2001, 123, 7180-7181.
29. Habaue, S.; Okamoto, Y.; Chem. Rec. 2001, 1, 46-52.
30. (a) Shibata, T.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 3609-3615.
31. (b) Miura, Y.; Shibata, T.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Am. Chem. Soc. 2006, 128, 16026-16027.
32. Wan, D.; Satoh, K.; Kamigaito, M. Macromolecules 2006, 39, 6882-6886.
33. (a) Hirano, T.; Miki, H.; Seno, M.; Sato, T. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 4404-4408.
34. (b) Hirano, T.; Miki, H.; Seno, M.; Sato, T. Polymer 2005, 46, 3693-3699.
35. (c) Hirano, T.; Okumura, Y.; Kitajima, H.; Seno, M.; Sato, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4450-4460.
36. (d) Hirano, T.; Ishizu, H.; Seno, M.; Sato, T. Polymer 2005, 46, 10607-10610.
37. Hirano, T.; Ishizu, H.; Sato, T. Polymer 2008, 49, 438-445.
38. (a) Kamigaito, M. Satoh, K.; Wan. D.; Sugiyama, Y.; Koumura, K.; Shibata, T.; Okamoto, Y. ACS Symp. Ser. 2006, 944, 26-39.
39. (b) Kamigaito, M.; Satoh, K. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 6147-6158.
40. (c) Kamigaito, M.; Satoh, K. Macromolecules 2008, 41, 6147-6158.
41. (a) Kelly, T. R.; Kim. M. K, J. Am. Chem. Soc. 1994, 116, 7072-7080.
42. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
43. (c) Linton, B. R.; Goodman, M. S.; Hamilton, A. D. Chem. Eur. J. 2000, 6, 2449-2455.
44. (a) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261.
45. (b) Curran, D. P.; Kuo, L. H. Tetrahedron Lett. 1995, 36, 6647-6650.
46. (a) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299-4306.
47. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520-1543.
48. Thang, S. H.; Chong, Y. K.; Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 1999, 40, 2435-2438.
49. (a) Ray, B.; Isobe, Y.; Morioka, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2003, 36, 543-545.
50. (b) Ray, B.; Isobe, Y.; Matsumoto, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2004, 37, 1702-1710.
51. (c) Ray, B.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M.; Seno, M.; Kanaoka, S.; Aoshima, S. Polym. J. 2005, 37, 234-237.
52. Sugiyama, Y.; Satoh, K.; Kamigaito, M.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2086-2098.
53. Lutz, J.-F.; Neugebauer, D.; Matyjaszewski, K. J. Am. Chem. Soc. 2003, 125, 6986-6993.
54. Quinn, J. F.; Rizzardo, E.; Davis, T. P. Chem. Commun. 2001, 1044-1045.
55. Chiefari, J.; Mayadunne, R. T. A.; Moad, C. L.; Moad, G.; Rizzardo, E.; Postma, A.; Skidmore, M. A.; Thang, S. H. Macromolecules 2003, 36, 2273-2283.
56. (a) Wilcox, C. S.; Kim, E.-I.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621-634.
57. (b) Okino, T.; Yasutaka, H.; Furukawa, T.; Xu, X.; Y. Takemoto J. Am. Chem. Soc 2005, 127, 119-125.