Synthesis and structure of acyclic bis(ketenimine) complexes of zirconium

Organometallics

Volumn 17, Issue 7, 1998, Pages 1315-1323

  Rahim, Marufur ^a   Taylor, Nicholas J ^a   Xin, Shixuan ^a   Collins, Scott ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000000845     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970862h     Document Type: Article

References (66)

1. For recent reviewe see: (a) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Reiger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255.
2. For recent reviewe see: (a) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Reiger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255.
3. (a) Okuda, J. Chem. Ber. 1990, 123, 1644.
4. (b) Canich, J. A. (Exxon) Eur. Pat. Appl. EP-420-436 A1, April 4, 1991.
5. (c) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Y. (Dow) Eur. Pat. Appl. EP-416-815-A2, March 13, 1991.
6. (d) Kucht. A.; Kucht, H.; Barry, S.; Chein, J. C. W.; Rausch, M. D. Organometallics 1993, 12, 3075.
7. (e) Kucht, H.; Kucht, A.; Chien, J. C. W.; Rausch, M. D. Appl. Organomet. Chem. 1994, 8, 393.
8. (f) Gillis, D. J.; Tudoret, M.-J.; Baird, M. C. J. Am. Chem. Soc. 1993, 115, 2543.
9. (g) Quyoum, R.; Wang, Q.; Tudoret, M.-J.; Baird, M. C.; Gillis, D. J. J. Am. Chem. Soc. 1994, 116, 6435.
10. (h) Wang, Q.; Quyoum, R.; Gills, D. J.; Tudoret, M.-J.; Jeremic, D.; Hunter, B. K.; Baird, M. C. Organometallics 1996, 15, 693.
11. (a) Uhrhammer, R.; Black, D. G.; Gardner, T. G.; Olsen, J. D.; Jordan, D. C. J. Am. Chem. Soc. 1993, 115, 8493.
12. (b) Black, D. G.; Swenson, D. C.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3539.
13. (c) Crowther, D. J.; Baenziger, N. C.; Jordan, R. F. J. Chem. Soc., Chem. Commun. 1994, 2607.
14. (d) Kreuder, C.; Jordan, R. F.; Zhang, H. Organometallics 1995, 14, 2993.
15. (e) Rodriguez, G.; Bazan, G. C. J. Am. Chem. Soc. 1997, 119, 343.
16. (f) Bazan, G. C.; Rodriguez, G.; Cleary, B. P. J. Am. Chem. Soc. 1994, 116, 2177.
17. (g) Guan, R. W.; Bazan, G. C.; Kiely, A. F.; Schaefer, W. P.; Bercow, J. E. J. Am. Chem. Soc. 1994, 116, 4489.
18. (a) Scollard, J. D.; McConville, D. H. J. Am. Chem. Soc. 1996, 118, 10008.
19. (b) Scollard, J. D.; McConville, D. H.; Vittal, J. J. Organometallics 1995, 14, 5478.
20. (a) Gomez, R.; Green, M. L. H.; Haggizz, J. L. J. Chem. Soc., Chem. Commun. 1994, 2607.
21. (b) Duchateau, R.; Cornelis, T. W.; Meetsma, A.; van Duijnen, P. T.; Teuben, J. H. Organometallics 1996, 15, 2279.
22. (c) Herskovics-Korine, D.; Eisen, M. S. J. Organomet. Chem. 1995, 503, 307.
23. (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469.
24. (b) Cozz, P. G.; Gallo, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4994.
25. See e.g.: McGeaehin, S. G. Can. J. Chem. 1968, 46, 1903 and references therein.
26. We have screened a number of the complexes reported here in olefin polymerization, and the results will be reported elsewhere: Rahim, M.; Collins, S. Manuscript in preparation.
27. (a) Hitchcock, P. B.; Lappert, M. F.; Liu, D.-S. J. Chem. Soc., Chem. Commun. 1994, 2637.
28. (b) Lappert, M. F.; Liu, D.-S. J. Organomet. Chem. 1995, 500, 203.
29. (a) Pellecchia, C.; Grassi, A.; Immirzi, A. J. Am. Chem. Soc. 1993, 115, 1160.
30. (b) Pellecchia, C.; Grassi, A.; Zambelli, A. J. Mol. Catal. 1993,82, 57.
31. (c) Pellecchia, C.; Immirzi, A.; Grassi, A.; Zambelli, A. Organometallics 1994, 13, 298.
32. (d) Pellecchia, C.; Grassi, A.; Zambelli, A. Organometallics 1993, 12, 3856.
33. (a) Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
34. (b) Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936.
35. (c) Gauthier, W. J.; Corrigan, J. F.; Taylor, N. J.; Collins, S. Macromolecules 1995, 28, 3771.
36. Kim, I.; Jordan, R. F. Macromolecules 1996, 29, 489.
37. -1) for rotation about the Zr-N bond.
38. The fact that this high-field doublet is integrated to only two protons also implies that rotation about the N-Ph bond is hindered in 2d at 200 K, and in the case of 2b, this same process is slow on the NMR time scale even at room temperature.
39. (a) Bailar, J. C. J. Inorg. Nucl. Chem. 1958, 8, 165.
40. (b) Wentworth, R. A. D. Coord. Chem. Rev. 1972, 9, 171.
41. (c) Fleischer, E. B.; Gebala, A. E.; Swift, D. R.; Tasker, P. A. Inorg. Chem. 1972, 11, 2775.
42. (d) Churchill, M. R.; Reis, A. H. Inorg. Chem. 1972, 11, 1811.
43. (e) Vanquickenborne, L. G.; Pierloot, K. Inorg. Chem. 1981, 20, 3673.
44. (f) Darensbonrg, D. J.; Kump, R. L. Inorg. Chem. 1984, 23, 2993.
45. Bushweller C. H.; Letenare, L. J.; Brunelle, J. A.; Bilorsky, H. J.; Whalon, M. J.; Fiels, S. H. Calculation of Chemically Exchanging Spectra; (QCPE Program No. 466; Department of Chemistry, University of Vermont, Burlington, VT 05401.
46. Although we cannot rule out a dissociative process for the fluxional behavior, the observation that the barrier to interconversion for the bis(dimethylamido) complex 2b is higher (i.e. slow exchange on the NMR time scale at 298 K) than that in 2d seems inconsistent with a dissociative process; the trans effect of the dimethylamido ligands in 2b should facilitate dissociation of the bis(ketenimine) ligand.
47. (a) O'Connor, J. M.; Casey, C. P. Chem. Rev. (Washington, D.C.) 1987, 87, 307.
48. (b) Rerek, M. E.; Basolo, F. J. Am. Chem. Soc. 1984, 106, 5908.
49. (c) Ji, L.-N.; Rerek, M. E.; Basolo, F. Organometallics 1984, 3, 740.
50. Rausch, M. D.; Moriarty, K. J.; Atwood, J. L.; Hunter, W. E.; Samuel, E. J. Organomet. Chem. 1987, 327, 39.
51. (a) Jeffery, J.; Lappert, M. F.; Luong-Thi, N. T.; Webb, M. J. Chem. Soc., Dalton Trans. 1981, 1593.
52. (b) Prout, K.; Cameron, T. S.; Forder, R. A.; Critchley, S. R.; Denton, B.; Ress, G. V. Acta Crystallogr. 1974, B30, 2290.
53. (c) Lauer, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
54. (d) Sikora, D. J.; Rausch, M. D.; Rogers, R. D.; Atwood, J. L. J. Am. Chem. Soc. 1981, 103, 1265.
55. (e) Bush, M. A.; Sinn, G. A. J. Chem. Soc. A 1971, 2225.
56. The nitrogen atoms in the acyclic bis(ketenimine) ligand will lower the energy of the π-orbitals on N, and indirectly those on adjacent C atoms, compared with an analogous all-C π system.
57. (a) Ernst, R. D. Chem. Rev. 1988, 88, 1255.
58. (b) Bleeke, J. R.; Earl, P. L. Organometallics 1989, 8, 2735.
59. (c) Freeman, J. W.; Hallinan, N. C.; Arif, A. M.; Gedridge, R. W.; Ernst, R. D.; Basolo, F. J. Am. Chem. Soc. 1991, 113, 6509.
60. (d) Hyla-Kryspin, I.; Waldman, T. E.; Meleridez, E.; Trakarnpruk, W.; Arif, A. M.; Ziegler, M. L.; Ernst, R. D.; Gleiter, R. Organometallics 1995, 14, 5030.
61. (a) Zucchini, U.; Albizzati, E.; Giannini, U. J. Organomet. Chem. 1971, 26, 357.
62. (b) Davidson, P. J.; Lappert, M. F.; Pearce, R. J. Organomet. Chem. 1973, 57, 269.
63. (a) Bradley, D. C.; Thomas, I. M. Proc. Chem. Soc., London 1959, 225.
64. (b) Bradley, D. C.; Thomas, I. M. Proc. Chem. Soc., London 1960, 3857.
65. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. 4.
66. Stewart, R. F.; Davidson, E. R.; Simpson, W. T. J. Chem. Phys. 1965, 42, 3175.