Mechanistic studies of nickel(II) alkyl agostic cations and alkyl ethylene complexes: Investigations of chain propagation and isomerization in (α-diimine)Ni(II)-catalyzed ethylene polymerization

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 3068-3081

  Leatherman, Mark D ^a   Svejda, Steven A ^a   Johnson, Lynda K ^a   Brookhart, Maurice ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

PRECURSORS;

ALKYLATION; COMPLEXATION; CROSSLINKING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

CATION; ETHYLENE DERIVATIVE; NICKEL COMPLEX; PALLADIUM; POLYETHYLENE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ISOMERISM; LOW TEMPERATURE; METAL BINDING; MODEL; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PRESSURE; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0037433508     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021071w     Document Type: Article

References (57)

1. Keim, W.; Appel, R.; Storeck, A.; Kruger, C.; Goddard, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 116-117.
2. Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 1001-1003.
3. Ostoja Starzewski, K. A.; Witte, J. Angew. Chem. 1985, 97, 610-612.
4. Klabunde, U.; Ittel, S. D. J. Mol. Catal. 1987, 41, 123-134.
5. Brookhart, M.; DeSimone, J. M.; Grant, B. E.; Tanner, M. J. Macromolecules 1995, 28, 5378-5380.
6. Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049-4050.
7. Small, B. L.; Brookhart, M. Macromolecules 1999, 32, 2120-2130.
8. Britovsek, G. J. P.; Gibson, V. C.; Kimberly, B. S.; Maddox, P. J.; McTravish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849-850.
9. Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 429-447.
10. Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedrich, S. K.; Grubbs, R. H.; Bansleben, D. A. Science 2000, 287, 460-462.
11. Hicks, F. A.; Brookhart, M. Organometallics 2001, 20, 3217-3219.
12. Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169-1203.
13. Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414-6415.
14. Gates, D. P.; Svejda, S. A.; Oñate, E.; Killian, C. M.; Johnson, L. K.; White, P. S.; Brookhart, M. Macromolecules 2000, 33, 2320-2334.
15. Brookhart, M. S.; Johnson, L. K.; Killian, C. M.; Arthur, S. D.; Feldman, J.; McCord, E. F.; McLain, S. J.; Kreutzer, K. A.; Bennett, A. M. A.; Coughlin, E. B.; Ittel, S. D.; Parthasarathy, A.; Tempel, D. J. WO Patent Application 9623010 to DuPont, April 3, 1995.
16. McLain, S. J.; Feldman, J.; McCord, E. F.; Gardner, K. H.; Teasley, M. F.; Coughlin, E. B.; Sweetman, K. J.; Johnson, L. K.; Brookhart, M. Macromolecules 1998, 31, 6705-6707.
17. Guan, Z.; Cotts, P. M.; McCord, E. F.; McLain, S. J. Science 1999, 283, 2059-2062.
18. Cotts, P. M.; Guan, Z.; McCord, E. F.; McLain, S. J. Macromolecules 2000, 33, 6945-6952.
19. McCord, E. F.; McLain, S. J.; Nelson, L. T. J.; Arthur, S. D.; Coughlin, E. B.; Ittel, S. D.; Johnson, L. K.; Tempel, D. J.; Killian, C. M.; Brookhart, M. Macromolecules 2001, 34, 362-371.
20. Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 267-268.
21. Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888-899.
22. Johnson, L.; Bennett, A.; Dobbs, K.; Hauptman, E.; Ionkin, A.; Ittel, S.; McCord, E.; McLain, S.; Radzewich, C.; Yin, Z.; Wang, L.; Wang, Y.; Brookhart, M. Polym. Mater. Sci. Eng. 2002, 86, 319.
23. McLain, S. J.; Sweetman, K. J.; Johnson, L. K.; McCord, E. F. Polym. Mater. Sci. Eng. 2002, 86, 320-321.
24. Killian, C. M.; Johnson, L. K.; Brookhart, M. Organometallics 1997, 16, 2005-2007.
25. Tempel, D. J. Ph.D. Dissertation, University of North Carolina at Chapel Hill, 1998.
26. Svejda, S. A.; Brookhart, M. Organometallics 1999, 18, 65-74.
27. Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 11664-11665.
28. Gottfried, A. C.; Brookhart, M. Macromolecules 2001, 34, 1140-1142.
29. Leatherman, M. D.; Brookhart, M. Macromolecules 2001, 34, 2748-2750.
30. Killian, C. M. Ph.D. Dissertation, University of North Carolina at Chapel Hill, 1996.
31. Tempel, D. J.; Brookhart, M. Organometallics 1998, 17, 2290-2296.
32. Svejda, S. A.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 10634-10635.
33. Tempel, D. J.; Johnson, L. K.; Huff, R. L.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6686-6700.
34. Shultz, L. H.; Tempel, D. J.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 11539-11555.
35. Shultz, L. H.; Brookhart, M. Organometallics 2001, 20, 3975-3982.
36. Musaev, D. G.; Froese, R. D. J.; Svensson, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 367-374.
37. Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177-6186.
38. 1H NMR spectra, the resonance for the methine hydrogen in the Pd(isopropyl)agostic complex is obscured by ligand resonances; thus quantitative analysis of its dynamic behavior cannot be determined. Therefore, the barrier obtained in the similar Pd ethyl agostic species is used as an approximation in this analysis.
39. 1H NMR spectrum.
40. Espenson, J. H. Chemical Kinetics and Reaction Mechanisms; McGraw-Hill: New York, 1981.
41. 2 in a nonkinetic ratio supports this contention.
42. Carr, N.; Mole, L.; Orpen, A. G.; Spencer, J. L. J. Chem. Soc., Dalton Trans. 1992, 2653-2662.
43. Mole, L.; Spencer, J. L.; Carr, N.; Orpen, A. G. Organometallics 1991, 10, 49-52.
44. Conroy-Lewis, F. M.; Mole, L.; Redhouse, A. D.; Litster, S. A.; Spencer, J. L. J. Chem. Soc., Chem. Commun. 1991, 1601-1603.
45. Deng, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 1094-1100.
46. Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581-1587.
47. Density functional calculations suggest a concerted β-H elimination/olefin rotation/reinsertion process rather than a stepwise mechanism: Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 1094-1100.
48. Woo, T. K.; Blöchl, P. E.; Ziegler, T. J. Phys. Chem. A 2000, 104, 121-129.
49. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
50. van Asselt, R.; Elsevier, C. J.; Smeets, W. J. J.; Spek, A. L.; Benedix, R. Recl. Trav. Chim. Pays-Bas 1994, 113, 88-98.
51. Tom Dieck, H.; Svoboda, M.; Grieser, T. Z. Naturforsch. 1981, 36b, 823-832.
52. Svoboda, M.; Tom Dieck, H. J. Organomet. Chem. 1980, 191, 321-328.
53. Ward, L. G. L. Inorg. Synth. 1971, 13, 154-164.
54. Brookhart, M.; Grant, B.; Volpe, A. F. Organometallics 1992. 11, 3920-3922.
55. White, P. A.; Calabrese, J.; Theopold, K. H. Organometallics 1996, 15, 5473-5475.
56. Siegel, J. S.; Anet, F. A. J. Org. Chem. 1988, 53, 2629-2630.
57. 2F.