Sulfonyl chlorides as initiators for the ruthenium-mediated living radical polymerization of methyl methacrylate

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 34, Issue 17, 1996, Pages 3585-3589

  Matsuyama, Mutsuhiro ^a   Kamigaito, Masami ^a   Sawamoto, Mitsuo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Living polymerization; Methyl methacrylate; Radical polymerization; Ruthenium complex; Sulfonyl chlorides

Indexed keywords

CATALYSTS; INITIATORS (CHEMICAL); MOLECULAR WEIGHT DISTRIBUTION; MONOMERS; POLYMERIZATION; RUTHENIUM COMPOUNDS; STYRENE; SYNTHESIS (CHEMICAL); TRANSITION METAL COMPOUNDS;

HOMOLYTIC CLEAVAGE; LIVING RADICAL POLYMERIZATION; SULFONYL CHLORIDES;

POLYMETHYL METHACRYLATES;

EID: 0030417747     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(199612)34:17<3585::AID-POLA13>3.0.CO;2-A     Document Type: Article

References (37)

1. For recent reviews on living/controlled radical polymerizations, see: (a) K. Matyjaszewski, S. Gaynor, D. Greszta, D. Mardare, and T. Shigemoto, J. Phys. Org. Chem., 8, 306 (1995); (b) T. P. Davis and D. M. Haddleton, in New Methods of Polymer Synthesis, Vol. 2, J. R. Ebdon and G. C. Eastmond, Eds., Blackie, Glasgow, 1995, pp. 1-36; (c) M. Sawamoto and M. Kamigaito, in Materials Science and Technology, Volume Polymer Synthesis, VCH, in preparation.
2. For recent reviews on living/controlled radical polymerizations, see: (a) K. Matyjaszewski, S. Gaynor, D. Greszta, D. Mardare, and T. Shigemoto, J. Phys. Org. Chem., 8, 306 (1995); (b) T. P. Davis and D. M. Haddleton, in New Methods of Polymer Synthesis, Vol. 2, J. R. Ebdon and G. C. Eastmond, Eds., Blackie, Glasgow, 1995, pp. 1-36; (c) M. Sawamoto and M. Kamigaito, in Materials Science and Technology, Volume Polymer Synthesis, VCH, in preparation.
3. For recent reviews on living/controlled radical polymerizations, see: (a) K. Matyjaszewski, S. Gaynor, D. Greszta, D. Mardare, and T. Shigemoto, J. Phys. Org. Chem., 8, 306 (1995); (b) T. P. Davis and D. M. Haddleton, in New Methods of Polymer Synthesis, Vol. 2, J. R. Ebdon and G. C. Eastmond, Eds., Blackie, Glasgow, 1995, pp. 1-36; (c) M. Sawamoto and M. Kamigaito, in Materials Science and Technology, Volume Polymer Synthesis, VCH, in preparation.
4. (a) T. Otsu and M. Yoshida, Makromol. Chem. Rapid Commun., 3, 127 (1982);
5. (b) T. Otsu, M. Yoshida, and T. Tazaki, Makromol. Chem. Rapid Commun., 3, 133 (1982).
6. D. H. Solomon, E. Rizzardo, and P. Cacioli, U.S. Pat. 4,581,429 (1986).
7. J. D. Druliner, Macromolecules, 24, 6079 (1991); J. Phys. Org. Chem., 8, 316 (1995).
8. J. D. Druliner, Macromolecules, 24, 6079 (1991); J. Phys. Org. Chem., 8, 316 (1995).
9. (a) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 2987, 5316 (1993);
10. (b) M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, and M. Saban, Macromolecules, 27, 7228 (1994);
11. (c) P. M. Kazmaier, K. A. Moffat, M. K. Georges, R. P. N. Veregin, and G. K. Hamer, Macromolecules, 28, 1841 (1995);
12. (d) R. P. N. Veregin, M. K. Georges, G. K. Hamer, and P. M. Kazmaier, Macromolecules, 28, 4391 (1995);
13. (e) M. K. Georges, R. A. Kee, R. P. N. Veregin, G. K. Hamer, and P. M. Kazmaier, J. Phys. Org. Chem., 8, 301 (1995);
14. (f) B. Keoshkerian, M. K. Georges, and D. Boils-Boissier, Macromolecules, 28, 6381 (1995);
15. (g) M. D. Saban, M. K. Georges, R. P. N. Veregin, G. K. Hamer, and P. M. Kazmaier, Macromolecules, 28, 7032 (1995).
16. C. J. Hawker, J. Am. Chem. Soc., 116, 11185 (1994); Macromolecules, 28, 2993 (1995); Angew. Chem., Int. Engl. Ed., 34, 1456 (1995).
17. C. J. Hawker, J. Am. Chem. Soc., 116, 11185 (1994); Macromolecules, 28, 2993 (1995); Angew. Chem., Int. Engl. Ed., 34, 1456 (1995).
18. C. J. Hawker, J. Am. Chem. Soc., 116, 11185 (1994); Macromolecules, 28, 2993 (1995); Angew. Chem., Int. Engl. Ed., 34, 1456 (1995).
19. (a) D. Mardare and K. Matyjaszewski, Macromol. Rapid Commun., 15, 37 (1994); Macromolecules, 27, 645 (1994);
20. (a) D. Mardare and K. Matyjaszewski, Macromol. Rapid Commun., 15, 37 (1994); Macromolecules, 27, 645 (1994);
21. (b) K. Matyjaszewski, S. Gaynor, and J.-S. Wang, Macromolecules, 28, 2093 (1995);
22. (c) I. Li, B. A. Howell, K. Matyjaszewski, T. Shigemoto, P. B. Smith, and D. B. Priddy, Macromolecules, 28, 6692 (1995).
23. J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995); Macromolecules, 28, 7572, 7901 (1995).
24. J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995); Macromolecules, 28, 7572, 7901 (1995).
25. M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Polym. Prepr. Jpn., 43(2), 255 (1994).
26. R. B. Wayland, G. Poszmik, S. L. Mukerjee, and M. Fryd, J. Am. Chem. Soc., 116, 7943 (1994).
27. (a) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995); Polym. Prepr. Jpn., 43(6), 1792 (1994);
28. (a) M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995); Polym. Prepr. Jpn., 43(6), 1792 (1994);
29. (b) M. Sawamoto, M. Kato, M. Kamigaito, and T. Higashimura, Polym. Prepr. Div. Polym. Chem. Am. Chem. Soc., 36(1), 539 (1995).
30. T. Ando, M. Kato, M. Kamigaito, and M. Sawamoto, Macromolecules, 29, 1070 (1996).
31. V. Percec and B. Barboiu, Macromolecules, 28, 7970 (1995).
32. C. J. Hawker and J. L. Hedrick, Macromolecules, 28, 2993 (1995).
33. N. Kamigata, H. Sawada, and M. Kobayashi, J. Org. Chem., 48, 3793 (1983).
34. (a) S. J. Cristol and J. A. Reeder, J. Org. Chem., 26, 2182 (1961);
35. (b) M. Asscher and D. Vofsi, J. Chem. Soc., 4962 (1964).
36. 1.15); Kyowa Chemical] (ca. 5 g) to remove the metal-containing residues. After the absorbent was separated by filtration (Whatman 113V), the filtrate was washed with water and evaporated to dryness to give the products, which were subsequently vacuum dried overnight.
37. n = 1.06-1.22).