Copolymerization of ethylene and propylene with functionalized vinyl monomers by palladium(II) catalysts

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 267-268

  Johnson, Lynda K ^a   Mecking, Stefan ^a   Brookhart, Maurice ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0142070493     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953247i     Document Type: Article

References (28)

1. As leading references, see: (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. (b) Yang, X.: Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994. 116, 10015-10031. (c) Coughlin. E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607. (d) Crowther, D. J.; Baenziger, N- C ; Jordan, R. F J. Am. Chem. Soc. 1991, 113, 1455-1457. (e) Kaminsky, W.; Kulper, K.; Brintzinger, H. H,: Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-508. (f) Ewen, J. A. J Am. Chem. Soc. 1984, 706, 6355-6364,
2. As leading references, see: (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. (b) Yang, X.: Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994. 116, 10015-10031. (c) Coughlin. E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607. (d) Crowther, D. J.; Baenziger, N- C ; Jordan, R. F J. Am. Chem. Soc. 1991, 113, 1455-1457. (e) Kaminsky, W.; Kulper, K.; Brintzinger, H. H,: Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-508. (f) Ewen, J. A. J Am. Chem. Soc. 1984, 706, 6355-6364,
3. As leading references, see: (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. (b) Yang, X.: Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994. 116, 10015-10031. (c) Coughlin. E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607. (d) Crowther, D. J.; Baenziger, N- C ; Jordan, R. F J. Am. Chem. Soc. 1991, 113, 1455-1457. (e) Kaminsky, W.; Kulper, K.; Brintzinger, H. H,: Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-508. (f) Ewen, J. A. J Am. Chem. Soc. 1984, 706, 6355-6364,
4. As leading references, see: (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. (b) Yang, X.: Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994. 116, 10015-10031. (c) Coughlin. E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607. (d) Crowther, D. J.; Baenziger, N- C ; Jordan, R. F J. Am. Chem. Soc. 1991, 113, 1455-1457. (e) Kaminsky, W.; Kulper, K.; Brintzinger, H. H,: Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-508. (f) Ewen, J. A. J Am. Chem. Soc. 1984, 706, 6355-6364,
5. As leading references, see: (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. (b) Yang, X.: Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994. 116, 10015-10031. (c) Coughlin. E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607. (d) Crowther, D. J.; Baenziger, N- C ; Jordan, R. F J. Am. Chem. Soc. 1991, 113, 1455-1457. (e) Kaminsky, W.; Kulper, K.; Brintzinger, H. H,: Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-508. (f) Ewen, J. A. J Am. Chem. Soc. 1984, 706, 6355-6364,
6. As leading references, see: (a) Coates, G. W.; Waymouth, R. M. Science 1995, 267, 217-219. (b) Yang, X.: Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994. 116, 10015-10031. (c) Coughlin. E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607. (d) Crowther, D. J.; Baenziger, N- C ; Jordan, R. F J. Am. Chem. Soc. 1991, 113, 1455-1457. (e) Kaminsky, W.; Kulper, K.; Brintzinger, H. H,: Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507-508. (f) Ewen, J. A. J Am. Chem. Soc. 1984, 706, 6355-6364,
7. Polymerization of olefins containing functional groups in a position remote from the vinyl group by early transition metal catalysts has been reported: (a) Chung, T. C. Macromolecules 1988, 21, 865-869. (b) Chung, T. C.; Rhubright, D. Macromolecules 1993, 26, 3019-3025. (c) Kesti, M. R.: Coates, G. W.; Waymouth. R. M. J. Am. Chem. Soc. 1992, 114, 9679-9680.
8. Polymerization of olefins containing functional groups in a position remote from the vinyl group by early transition metal catalysts has been reported: (a) Chung, T. C. Macromolecules 1988, 21, 865-869. (b) Chung, T. C.; Rhubright, D. Macromolecules 1993, 26, 3019-3025. (c) Kesti, M. R.: Coates, G. W.; Waymouth. R. M. J. Am. Chem. Soc. 1992, 114, 9679-9680.
9. Polymerization of olefins containing functional groups in a position remote from the vinyl group by early transition metal catalysts has been reported: (a) Chung, T. C. Macromolecules 1988, 21, 865-869. (b) Chung, T. C.; Rhubright, D. Macromolecules 1993, 26, 3019-3025. (c) Kesti, M. R.: Coates, G. W.; Waymouth. R. M. J. Am. Chem. Soc. 1992, 114, 9679-9680.
10. (a) Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137-1138.
11. (b) Peuckert, M.; Keim, W. Organometallics 1983, 2, 594-597.
12. (c) Wilke. G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185-206.
13. Polymerization of ethylene has been described: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horvath, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634-5636. (c) Keim, W.; Kowaldt, F. H.; Goddard, R,; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466-467. (d) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134. (e) Wang, L.; Lu, R. S.: Bau, R.: Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000. Certain Ni(II) catalysts convert α-olefins to oligomers with degrees of polymerization of ∼4-20: (f) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
14. Polymerization of ethylene has been described: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horvath, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634-5636. (c) Keim, W.; Kowaldt, F. H.; Goddard, R,; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466-467. (d) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134. (e) Wang, L.; Lu, R. S.: Bau, R.: Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000. Certain Ni(II) catalysts convert α-olefins to oligomers with degrees of polymerization of ∼4-20: (f) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
15. Polymerization of ethylene has been described: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horvath, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634-5636. (c) Keim, W.; Kowaldt, F. H.; Goddard, R,; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466-467. (d) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134. (e) Wang, L.; Lu, R. S.: Bau, R.: Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000. Certain Ni(II) catalysts convert α-olefins to oligomers with degrees of polymerization of ∼4-20: (f) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
16. Polymerization of ethylene has been described: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horvath, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634-5636. (c) Keim, W.; Kowaldt, F. H.; Goddard, R,; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466-467. (d) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134. (e) Wang, L.; Lu, R. S.: Bau, R.: Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000. Certain Ni(II) catalysts convert α-olefins to oligomers with degrees of polymerization of ∼4-20: (f) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
17. Polymerization of ethylene has been described: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horvath, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634-5636. (c) Keim, W.; Kowaldt, F. H.; Goddard, R,; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466-467. (d) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134. (e) Wang, L.; Lu, R. S.: Bau, R.: Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000. Certain Ni(II) catalysts convert α-olefins to oligomers with degrees of polymerization of ∼4-20: (f) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
18. Polymerization of ethylene has been described: (a) Schmidt, G. F.; Brookhart, M. J. Am. Chem. Soc. 1985, 107, 1443-1444. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horvath, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634-5636. (c) Keim, W.; Kowaldt, F. H.; Goddard, R,; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466-467. (d) Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134. (e) Wang, L.; Lu, R. S.: Bau, R.: Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000. Certain Ni(II) catalysts convert α-olefins to oligomers with degrees of polymerization of ∼4-20: (f) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
19. Doak, K. W. In Encyclopedia of Polymer Science and Engineering: Mark. H. F., Ed.; John Wiley and Sons: New York, 1986; Vol. 6, pp 386-429.
20. n ≤ 4100), but no detailed product characterizations were given: Drent, E.; Pello, D. H. L.; Jager, W. W. Eur. Pat. Appl. 589527, 1994.
21. Johnson, L. K.; Killian, C. M.: Brookhart M. J. Am. Chem. Soc. 1995, 117, 6414-6415.
22. For complete data, cf. supporting information.
23. C(O)OR carbon atoms are excluded.
24. 13C NMR spectroscopy supports the proposed copolymer structure: McCord. E.; McLain, S., unpublished results.
25. 9 This implies 2,1-insertion of propylene and subsequent "chain straightening" by chain migration to the terminal carbon atom.
26. Mecking, S.: Brookhart. M., unpublished results.
27. 8
28. The more facile substitution of the carbonyl group of the fluorinated chelate by ethylene may be partially responsible for the higher productivities in the FOA copolymerizations.