Ring-opening polymerization of heterocycles with palladium insertion catalysts: Observation of a multifunctional polymerization initiator

Organometallics

Volumn 18, Issue 20, 1999, Pages 3953-3955

  Lim, Ngiap Kie ^a   Yaccato, Karin J ^a   Dghaym, Rania D ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001499481     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990265q     Document Type: Article

References (27)

1. For reviews, see: (a) Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996. (b) Ring-Opening Polymerization; Brunelle, D. J., Ed.; Hanser: Munich, 1993. (c) Yagci, Y.; Mishra, M. K. In Macromolecular Design: Concept and Practice; Mishra, M. K., Ed.; Polymer Frontiers: New York, 1994; p 391.
2. For reviews, see: (a) Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996. (b) Ring-Opening Polymerization; Brunelle, D. J., Ed.; Hanser: Munich, 1993. (c) Yagci, Y.; Mishra, M. K. In Macromolecular Design: Concept and Practice; Mishra, M. K., Ed.; Polymer Frontiers: New York, 1994; p 391.
3. For reviews, see: (a) Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996. (b) Ring-Opening Polymerization; Brunelle, D. J., Ed.; Hanser: Munich, 1993. (c) Yagci, Y.; Mishra, M. K. In Macromolecular Design: Concept and Practice; Mishra, M. K., Ed.; Polymer Frontiers: New York, 1994; p 391.
4. (a) Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
5. (b) Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663.
6. (c) Abu-Surrah, A. S.; Rieger, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2475.
7. For examples, see: (a) Nakano, T.; Okamoto, Y.; Hatada, K. J. Am. Chem. Soc. 1992, 114, 1318. (b) Novak, B. M.; Goodwin, A. A.; Patten, T. E.; Deming, T. J. Polym. Prepr. 1996, 37, 446.
8. For examples, see: (a) Nakano, T.; Okamoto, Y.; Hatada, K. J. Am. Chem. Soc. 1992, 114, 1318. (b) Novak, B. M.; Goodwin, A. A.; Patten, T. E.; Deming, T. J. Polym. Prepr. 1996, 37, 446.
9. Bisht, K. S.; Deng, F.; Gross, R. A.; Kaplan, D. L.; Swift, G. J. Am. Chem. Soc. 1998, 120, 1363.
10. Aida, T.; Inoue, S. J. Am. Chem. Soc. 1988, 107, 1358.
11. Yasuda, H.; Tamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134.
12. (a) Dghaym, R. D.; Yaccato, K. J.; Arndtsen, B. A. Organometallics 1998, 17, 4.
13. (b) van Asselt, R.; Gielens, E. E. C. G.; Rulke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
14. 13C NMR peaks noted were those of the polymer.
15. For examples of cationic and insertion polymerization catalysts, see: Hayakawa, M.; Mitani, M.; Yamada, T.; Mukaiyama, T. Macromol. Rapid Commun. 1996, 17, 865. Quyoum, R.; Wang, Q.; Tudoret, M. J.; Baird, M. C. J. Am. Chem. Soc. 1994, 116, 6435.
16. For examples of cationic and insertion polymerization catalysts, see: Hayakawa, M.; Mitani, M.; Yamada, T.; Mukaiyama, T. Macromol. Rapid Commun. 1996, 17, 865. Quyoum, R.; Wang, Q.; Tudoret, M. J.; Baird, M. C. J. Am. Chem. Soc. 1994, 116, 6435.
17. 1H NMR of 9: δ 2.82 (d, 3H), 7.70 (t, 2H), 8.19 (t, 2H), 8.48 (d, 2H), 8.57 (d, 2H).
18. -: δ 2.38 (s, 3H), 4.16 (s, 3H), 7.2-7.8 (m, 9H), 9.30 (s, 1H).
19. n from GPC data. For complete polymer characterization, see the Supporting Information.
20. + end group: δ 2.49 (s, 3H), 3.76 (s, 3H), 4.20 (t, 2H), 7.2-7.8 (m, 4H), 9.15 (s, 1H).
21. -1; δ 170.3 (CO).
22. Tanaka, M.; Koyanagi, M.; Kobayashi, T. Tetrahedron Lett. 1981, 22, 3875 and references therein.
23. Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195.
24. The role of CO insertion in path C could be to effect the Lewis acidity of palladium. Such ancillary ligand effects have been previously observed for THF ring opening: Borkowsky, S. L.; Jordan, R. F.; Hinch, G. D. Organometallics 1991, 10, 1268.
25. Markies, B. A.; Kruis, D.; Rietveld, M. H. P.; Verkerk, K. A. N.; Boersma, J.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 5263.
26. Organic initiators for simultaneous free radical and ring-opening polymerization have been recently prepared: (a) Weimer, M. W.; Scherman, O. A.; Sogah, D. Y. Macromolecules 1998, 31, 8425. (b) Mecerreyes, D.; Moineau, G.; Dobois, P.; Jerome, E.; Hedrick, J. L.; Hawker, C. J.; Malmstrom, K. E.; Trollsas, M. Angew. Chem., Int. Ed. 1998, 37, 1274.
27. Organic initiators for simultaneous free radical and ring-opening polymerization have been recently prepared: (a) Weimer, M. W.; Scherman, O. A.; Sogah, D. Y. Macromolecules 1998, 31, 8425. (b) Mecerreyes, D.; Moineau, G.; Dobois, P.; Jerome, E.; Hedrick, J. L.; Hawker, C. J.; Malmstrom, K. E.; Trollsas, M. Angew. Chem., Int. Ed. 1998, 37, 1274.