Controlled/“Living” Radical Polymerization. Halogen Atom Transfer Radical Polymerization Promoted by a Cu(I)/Cu(II) Redox Process

Macromolecules

Volumn 28, Issue 23, 1995, Pages 7901-7910

  Wang, Jin Shan ^a   Matyjaszewski, Krzysztof ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; CATALYSTS; CHEMICAL ANALYSIS; COPPER; FREE RADICALS; HALOGEN ELEMENTS; MONOMERS; REDOX REACTIONS; TRANSITION METALS;

ALKYL HALIDES; ATOM TRANSFER RADICAL ADDITION; ATOM TRANSFER RADICAL POLYMERIZATION; HALOGEN ATOM; STEREOCHEMISTRY;

FREE RADICAL POLYMERIZATION;

EID: 0029638116     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma00127a042     Document Type: Article

References (49)

1. For reviews of atom transfer methods in organic synthesis, see: Curran, D. P. Synthesis 1988, 489.
2. Curran, D. P. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer: Dordrecht, The Netherlands, 1989; p 37.
3. Curran, D. P. In Comprehensive Organic Synthesis, Trost, B. M. Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4, p 715.
4. Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
5. Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Toma, G. J. Am. Chem. Soc. 1994, 116, 4279.
6. Matyjaszewski, K.; Gaynor, S.; Wang, J. S. Macromolecules 1995, 28, 2093.
7. Gaynor, S.; Wang, J. S.; Matyjaszewski, K. Polym. Prep. (Am. Chem. Soc., Div. Polym. Chem.) 1995, 36, 467.
8. Wang, J. S.; Gaynor, S.; Matyjaszewski, K. Polym. Prep. (Am. Chem. Soc., Div. Polym. Chem.), 1995, 36, 465.
9. Bellus, D. Pure Appl. Chem. 1985, 57, 1827. and references cited therein.
10. Nagashima, H.; Ozaki, N., Ishii, M.; Seki, K.; Wakamatsu, H.; Itoh, K. J. Org. Chem. 1993, 58, 464.
11. Udding, J. H.; Tuijp, K. J. M.; van Zanden, M. N. A.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1994, 59, 1993.
12. Seijas, J. A.; Vazquez-Tato, M. P.; Castedo, L.; Estevez, R. J.; Onega, M. G.; Ruiz, M. Tetrahedron 1992, 48 (9), 1637.
13. Nagashima, H.; Wakamatsu, H.; Ozaki, N.; Ishii, T.; Watanabe, M.; Tajima, T.; Itoh, K. J. Org. Chem. 1992, 57, 1682.
14. Hayes, T. K.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533.
15. Hirao, T.; Ohshiro, Y. Synlett 1990, 217.
16. Hirao, T.; Fujii, T.; Ohshiro, Y.; Ikeda, I. J. Synth. Org. Chem. (Jpn.) 1994, 52 (3), 197.
17. Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519, and references cited therein.
18. Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
19. Matyjaszewski, K.; Wang, J. S. U.S. Patent pending.
20. Bamford, C. H. In Reactivity, Mechanism and Structure in Polymer Chemistry; Jenkins, A. D.; Ledwith, A., Eds.; Wiley: London, 1974; p 52.
21. Peat, I. R.; Reynolds, W. P. Tetrahedron Lett. 1972, 14, 1359.
22. Wang, J. S.; Warin, R.; Jerome, R.; Teyssie, Ph. Macromolecules 1993, 26, 5984.
23. Baumgarten, J. L.; Muller, A. H. E.; Hogen-Esch, T. E. Macromolecules 1991, 24, 353.
24. Danen, W. C. In Methods in Free Radical Chemistry, Huyser, E. L. S., Ed.; Dekker: New York, 1974; Vol. 5, p 1.
25. Poutsma, M. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, p 113.
26. Kato, M.; Kamigato, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721.
27. Wang, J. S.; Matyjaszewski, K. Unpublished results.
28. Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic Press: New York, 1978; and references cited therein.
29. Bamford, C. H. In Comprehensive Polymer Science; Allen, G., Aggarwal, S. L., Russo, S., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 3, p 123.
30. Bamford, C. H.; Eastmond, G. C.; Fildes, F. J. T. Proc. R. Soc. London 1972, A326, 431.
31. Boutevin, B.; Pietrasanta, Y. In Comprehensive Polymer Science; Allen, G., Aggarwal, S. L., Russo, S., Eds., Pergamon: Oxford, U. K., 1991; Vol. 3, p 185.
32. Szwarc, M. Nature 1956, 176, 1168.
33. Greszta, D.; Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 638.
34. Otsu, T.; Yoshida, M. Makromol. Chem., Rapid Commun. 1982, 3, 127, 133.
35. Endo, K.; Murata, K.; Otsu, T. Macromolecules 1992, 25, 5554.
36. Borsig, F.; Lazar, M.; Capla, M.; Florian, S. Angew. Makromol. Chem. 1969, 9, 89.
37. Bledzki, A.; Braun, D. Makromol. Chem. 1981, 182, 1047.
38. Druliner, J. D. Macromolecules 1991, 24, 6079.
39. Solomon, D. H.; Rizzardo, E.; Cacioli, P. U.S. Patent 4,581,429, March 27, 1985.
40. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
41. Mardare, D.; Matyjaszewski, K. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1994, 35, 778.
42. Hawker, C. J. J. Am. Chem. Soc., 1994, 116, 11185.
43. Li, I.; Howell, B. A.; Ellaboudy, A.; Kastl, P. E.; Priddy, D. B. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1994, 36, 469.
44. Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 645.
45. Wayland, B. B.; Poszmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943.
46. Burzyk, A. F.; O'Driscoll, K. F.; Rempel, G. L. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 3255.
47. Matyjaszewski, K. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 1995, 36, 541.
48. Bamford, C. H. In Comprehensive Polymer Science (First Supplement); Allen, G, Aggarwal, S. L., Russo, S., Eds.; Pergamon: Oxford, U.K., 1991; p 1.
49. Landini, D.; Rolla, F. J. Org. Chem. 1980, 45, 3527.