Rate constants for the trapping of various carbon-centered radicals by nitroxides: unimolecular initiators for living free radical polymerization

Macromolecules

Volumn 33, Issue 14, 2000, Pages 5065-5072

  Skene, W G ^a   Scaiano, J C ^a   Listigovers, Nancy A ^b   Kazmaier, Peter M ^b   Georges, Michael K ^b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b XEROX RESEARCH CENTRE OF CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL POLYMERIZATION; INITIATORS (CHEMICAL); PHOTOLYSIS; STYRENE; TEMPERATURE;

CARBON CENTERED RADICALS; LASER FLASH PHOTOLYSIS; UNIMOLECULAR INITIATORS;

NITROGEN OXIDES;

EID: 0034224126     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma991753c     Document Type: Article

References (69)

1. Nagashima, T.; Curran, D. P. Synlett 1996, 4, 330.
2. Dagonneau, M.; Kagan, E. S.; Mikhailov, V. I.; Rozantsev, E. G.; Sholle, V. D. Synthesis 1984, 11, 895.
3. Rychnovsky, S. D.; Vaidynanathan, R. J. Org. Chem. 1999, 64, 310.
4. Cella, J. A.; Kelley, J. A.; Kenehan, E. F. Tetrahedron Lett. 1975, 33, 2869.
5. Limoges, B.; Degrand, C. J. Electroanal. Chem. 1997, 422, 7.
6. Duz, A.; Onen, A.; Yagci, Y. Makromol. Chem. 1998, 258, 1.
7. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992.
8. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629.
9. Beckwith, A. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983.
10. Rizzardo, E.; Solomon, D. H. Polym. Bull. 1979, 1, 529.
11. Moad, G.; Rizzardo, E.; Solomon, D. H. Macromolecules 1982, 15, 909.
12. Moad, G.; Rizzardo, E.; Solomon, D. H. J. Macromol. Sci., Chem. 1982, A17, 51.
13. Moad, G.; Rizzardo, E.; Solomon, D. H. Polym. Bull. 1982, 6, 589.
14. Solomon, D. H.; Rizzardo, E.; Cacioli, P. US Patent 4,581,-429, 1986.
15. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
16. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K.; Saban, M. Macromolecules 1994, 27, 7228.
17. Stevens, M. P. Polymer Chemistry, An Introduction, 2nd ed.; Oxford University Press: New York, 1990; p 633.
18. Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185.
19. Skene, W. G.; Belt, S. T.; Connolly, T. C.; Hahn, P.; Scaiano, J. C. Macromolecules 1998, 31, 9103.
20. Baldovi, M. V.; Mohtat, N.; Scaiano, J. C. Macromolecules 1996, 29, 5497.
21. Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 7747.
22. Scaiano, J. C.; Tanner, M.; Weir, D. J. Am. Chem. Soc. 1985, 107, 4396.
23. Matyjaszewski, K.; Woodworth, B. E.; Zhang, X.; Gaynor, S. G.; Metzner, Z. Macromolecules 1998, 31, 5955.
24. Hawker, C. J.; Barclay, G. G.; Orellana, A.; Dao, J.; Devonport, W. Macromolecules 1996, 29, 5245.
25. Hawker, C. J.; Barclay, G. G.; Dao, J. J. Am. Chem. Soc. 1996, 118, 11467.
26. Ramey, C. E.; Luzzi, J. J. U.S. Patent 3,936,456, 1976,
27. Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904.
28. Baretz, B. H.; Turro, N. J. J. Am. Chem. Soc. 1983, 105, 1309.
29. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, 1991; p 628.
30. Skene, W. G.; Scaiano, J. C. J. Phys. Chem., in press.
31. Skene, W. G. Unpublished work.
32. Laidler, K. J.; Meiser, J. H. Physical Chemistry; The Benjamin/ Cummings Publishing Company, Inc.: Menlo Park, CA, 1982; p 919.
33. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper Collins Publishers: New York, 1987; p 1090.
34. Fischer, H. Macromolecules 1997, 30, 5666.
35. Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925.
36. Beckwith, A. L. J.; Bowry, V. W.; O'Leary, M.; Moad, G.; Rizzardo, E.; Solomon, D. H. J. Chem. Soc., Chem. Commun. 1986, 1003.
37. Catala, J. M.; Bubel, F.; Hammouch, S. O. Macromolecules 1995, 28, 8441.
38. Veregin, R. P. N.; Georges, M. K.; Hamer, G. K.; Kazmaier, P. M. Macromolecules 1995, 28, 4391.
39. Howell, B. A.; Priddy, D. B.; Li, I. Q.; Smith, P. B.; Kastl, P. E. Polym. Bull. 1996, 37, 451.
40. Steenbock, M.; Klapper, M.; Mullen, K.; Pinhal, N.; Hubrich, M. Acta Polym. 1996, 47, 276.
41. Greszta, D.; Matyjaszewski, K. Macromolecules 1996, 29, 7661.
42. Connolly, T. J.; Baldovi, M. V.; Mohtat, N.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4919.
43. Scaiano, J. C.; Connolly, T. J.; Mohtat, N.; Pliva, C. N. Can. J. Chem. 1997, 75, 92.
44. Korolenko, E. C.; Cozens, F. L.; Scaiano, J. C. J. Phys. Chem. 1995, 99, 14123.
45. Chatgilialoglu, C. In Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, FL, 1989; Vol. II, p 3.
46. Paul, H.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1978, 100, 4520.
47. Chong, Y. K.; Ercole, F.; Moad, G.; Rizzardo, E.; Thang, S. H.; Anderson, A. G. Macromolecules 1999, 32, 6895.
48. Odell, P. G.; Rabien, A.; Michalak, L. M.; Vergin, R. P. N.; Quinlan, M. H.; Moffat, K. A.; MacLeod, P. J.; Listigovers, N. A.; Honeyman, C. H.; Georges, M. K. Polym. Prepr. 1997, 38, 414.
49. Georges, M. K.; Listigovers, N. A.; Odell, P. G.; Hamer, G. K.; Quilan, M. H.; Veregin, R. P. N. Polym. Prepr. 1997, 38, 454.
50. MacLeod, P. J.; Georges, M. K.; Quinlan, M.; Moffat, K. A.; Listigovers, N. A. Polym. Prepr. 1997, 38, 459.
51. Keoshkerian, B.; Georges, M.; Quinlan, M.; Veregin, R.; Goodbrand, B. Macromolecules 1998, 31, 7559.
52. Goto, A.; Fukuda, T. Macromolecules 1999, 32, 618.
53. O'Neil, G. A.; Torkelson, J. M. Macromolecules 1999, 32, 411.
54. Rizzardo, E.; Serelis, A. K.; Solomon, D. H. Aust. J. Chem. 1982, 35, 2013.
55. de Leon, M. E.; Gnanou, Y.; Guerrero, R. Polym. Prepr. 1997, 38, 667.
56. A recent radiolytic study of the reaction of methyl methacrylate with OH radicals in aqueous solution observed similar signals: Wojnárovits, L.; Takács, E. Res. Chem. Intermed. 1999, 25, 275.
57. Lambert, J. B.; Shurvell, H. F.; Ligtner, D.; Cooks, R. G. Introduction to Organic Spectroscopy; Macmillan Publishing Company: New York, 1987; p 454.
58. Johnston, L. J.; Tencer, M.; Scaiano, J. C. J. Org. Chem. 1986, 51, 2806.
59. Lissi, E. A.; Encinas, M. V. In Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, FL, 1989; Vol. 2, p 111.
60. Green, S.; Fox, M. A. J. Phys. Chem. 1995, 99, 14752.
61. Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401.
62. Scaiano, J. C. Chem. Phys. Lett. 1981, 79, 441.
63. Connolly, T. J.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 1133.
64. Skene, W. G.; Scaiano, J. C. Polym. Prepr. 2000, 41, 163.
65. Skene, W. G.; Scaiano, J. C. Manuscript in preparation.
66. Engel, P. S. J. Am. Chem. Soc. 1970, 92, 6074.
67. Robbins, W. K.; Eastman, R. H. J. Am. Chem. Soc. 1970, 92, 6076.
68. Turro, N. J.; Gould, I. R.; Baretz, B. H. J. Phys. Chem. 1983, 87, 531.
69. Lunazzi, L.; Ingold, K. U.; Scaiano, J. C. J. Phys. Chem. 1983, 87, 529.