A novel construction of living polymerization by neighboring group participation: Living cationic ring-opening polymerization of a five-membered cyclic dithiocarbonate

Macromolecules

Volumn 31, Issue 25, 1998, Pages 9093-9095

  Choi, Wonmun ^a   Sanda, Fumio ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CATIONIC POLYMERIZATION; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR WEIGHT DISTRIBUTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING OPENING POLYMERIZATION;

LIVING POLYMERIZATION;

POLYCARBONATES;

EID: 0032294479     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9805102     Document Type: Article

References (33)

1. (a) Szwarc, M. Nature 1956, 778, 1168.
2. (b) Szwarc, M.; Levy, M.; Milkovich, R. J. Am. Chem. Soc. 1956, 78, 2656
3. (a) Aida, T.; Mizuta, R.; Yosida, Y.; Inoue, S. Makromol. Chem. 1981, 182, 1073
4. (b) Isoda, M.; Sugimoto, H.; Aida, T.; Inoue, S. Macromolecules 1997, 30, 57.
5. (a) Gilliom, L. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 733.
6. (b) Schrock, R. R.; Feldman, J.; Cannizo, L. F.; Wallace, K. C. Macromolecules 1987, 20, 1169.
7. (c) Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459.
8. (a) Georges, M. K.; Rizzardo, E.; Cacioli, P. M.; Harmer, G. K. Macromolecules 1993, 26, 2987.
9. (b) Greszta, D.; Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 638.
10. (c) Wayland, B. B.; Pszmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943.
11. (d) Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
12. (e) Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721.
13. (a) Miyamoto, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1984, 17, 265.
14. (b) Sawamoto, M.; Higashimura, T. Makromol. Chem., Symp. 1986, 3, 83.
15. (c) Katayama, H.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 3747.
16. (a) Faust, R.; Kennedy, J. P. Polym. Bull. 1986, 15, 317.
17. (b) Mishra, M. K.; Kennedy, J. P. J. Macromol. Sci. Chem. 1987, A24, 933.
18. (a) Faust, R.; Kennedy, J. P. Polym. Bull. 1988, 19, 21.
19. (b) Higashimura, T.; Ishihama, Y.; Sawamoto, M. Macromolecules 1993, 26, 744.
20. Higashimura, T.; Deng, Y. X. Polym. J. 1983, 15, 685.
21. (a) Vofsi, D.; Tobolsky, A. V. J. Polym. Sci., Part A. 1965, 3, 3261.
22. (b) Tezaka, Y.; Goethals, E. J. Eur. Polym. J. 1982, 18, 991.
23. Kobayashi, S.; Saegusa, T. Ring-Opening Polymerization; Ivin, K. J., Saegusa, T., Eds.; Elsevier: London, 1984; Vol. 2, p 761.
24. Choi, W. M.; Sanda, F.; Kihara, N.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 3853.
25. Choi, W.; Sanda, F.; Endo, T. Macromolecules 1998, 31, 2454.
26. (a) Goodman, L. Adv. Carbohydrate Chem. 1967, 22, 109.
27. (b) Paulsen, H. Adv. Carbohydrate Chem. 1971, 26, 127.
28. (c) Kobayashi, K.; Ichikawa, H.; Sumitomo, H. Macromolecules 1988, 21, 543.
29. Fotsch, C. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4141.
30. +).
31. 2): C, 51.95; H, 3.96; S, 25.21. Found: C, 51.37; H.; 4.23; S, 25.36.
32. 2Br groups were observed at 2.38 and 3.62 ppm with contents of 10.7 and 9.8 mol %, respectively.
33. 3 at room temperature, but the carbonyl carbon signal of the dithiocarbonic acid moiety slowly disappeared. The dithiocarbonic acid moiety of 3a′ (R′ = H) may be unstable to be transformed to thiol with releasing COS, which may affect the propagating end. This should be one reason for the broader molecular weight distribution of the polymer obtained with TfOH than that with TfOMe.