Living radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization) using dithiocarbamates as chain transfer agents

Macromolecules

Volumn 32, Issue 21, 1999, Pages 6977-6980

  Mayadunne, Roshan T A ^a   Rizzardo, Ezio ^a   Chiefari, John ^a   Chong, Yen Kwong ^a   Moad, Graeme ^a   Thang, San H ^a  

^a Nsiro MnlpFiilnr Sripnt   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AGENTS; AROMATIC COMPOUNDS; DERIVATIVES; MOLECULAR WEIGHT; NITROGEN COMPOUNDS; POLYESTERS; POLYSTYRENES; SULFUR COMPOUNDS;

DITHIOCARBAMATE; LIVING RADICAL POLYMERIZATION; POLYMETHACRYLATE ESTERS; REVERSIBLE ADDITION FRAGMENTATION CHAIN TRANSFER POLYMERIZATION;

FREE RADICAL POLYMERIZATION;

EID: 0033204692     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9906837     Document Type: Article

References (21)

1. Matyjaszewski, K. ACS Symp. Ser 1998, 685, 2-30.
2. Colombani, D. Prog. Polym. Sei. 1997, 22, 1649-1720.
3. Greszta, D.; Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 638-644.
4. Rizzardo, E.; Moad, G. In The Polymeric Materials Encyclopaedia: Synthesis, Properties and Applications; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; Vol. 5, p 3834.
5. Moad, G.; Ercole, F.; Johnson, C. H.; Krstina, J.; Moad, C. L.; Rizzardo, E.; Spurling, T. H.; Thang, S. H.; Anderson, A. G. ACS Symp. Ser 1998, 685, 332-360.
6. Otsu, T.; Matsumoto, A. Adv. Polym. Sei. 1998,136,75-137.
7. Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. Appl. WO 9801478 Al 980115 (Chem. Abstr. (1998) 128: 115390).
8. Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jefiery, J.; Le, T. P. T.; Mayadunne, R. T. A:; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559-5562.
9. Rizzardo, E.; Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Thang, S. H. Macromol. Symp., in press.
10. Chong, Y. K.; Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1999, 32, 2071-2074.
11. Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. Appl. WO 99/31144.
12. (a) Otsu, T.; Yoshida, M.; Kuriyama, A. Polytn. Bull. 1982, 7,45-50.
13. (b) Otsu, T.; Matsunaga, T.; Doi, T.; Matumoto, A. Eur. Polym. J. 1995, 31, 67-78.
14. (a) Moad, G.; Rizzardo, E.; Thang, S. H.-PCT Int. Appl. WO99/ 05099.
15. (b) Thang, S. H.; Chong, Y. K.; Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 1999, 2435-2438.
16. (a) For example, the transfer constant of S-benzyl NJfdiethyldithiocarbamate (2) in styrène polymerization has been measured as 0.009 at 80 °C (unpublished results from these laboratories)
17. (b) Lambrinos, P.; Tardi, M.; Polton, A.; Sigwalt, P. Eur. Polym. J. 1990,26, 1125-1135.
18. Doi, T.; Matsumoto, A.; Otsu, T. J. Polym. Sei., Part A: Polym. Chem. 1994, 32, 2911-2918.
19. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983.
20. It is well-known that the carbonyl group in amides and carbamates is polarized due to conjugation of the nonbonded electrons on nitrogen (see ref 15). Mathematical calculations conducted in our laboratory (unpublished data) and other published mathematical data (Hadad, C. H.; Rablen, P. R.; Wiberg, K. B. J. Org. Chem. 1998, 63, 8668-8681 and references there in) reveal that such polarization is much greater in the case of dithiocarbamates.
21. Katritzky, A. R.; Marson, C. M.; Faid-Allah, H. Heterocycles 1987, 26, 1657-1669.