Measurement of barriers for alkene dissociation and for inversion at zirconium in a d0 zirconium-alkyl-alkene complex

Organometallics

Volumn 19, Issue 19, 2000, Pages 3970-3977

  Casey, Charles P ^a   Carpenetti II, Donald W ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; COMPLEXATION; DECOMPOSITION; DISSOCIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; THERMODYNAMIC STABILITY; ZIRCONIUM COMPOUNDS;

DECOMPLEXATION; EPIMERIZATION; LINE SHAPE ANALYSIS;

ORGANOMETALLICS;

EID: 0034683314     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9908940     Document Type: Article

References (50)

1. (a) Cessee, P. J. Catal. 1964, 3, 80.
2. (b) Arlman, E. J.; Cossee, P. J. Catal. 1964, 3, 99.
3. (c) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1.
4. (d) Brookhart, M.; Volpe, A. F.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634.
5. (e) Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
6. (f) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K. J. Chem. Soc., Chem. Commun. 1982, 1410.
7. (g) Ivin, K. J.; Rooney, J. J.; Stewart, C. D.; Green, M. L. H.; Mahtab, R. J. Chem. Soc., Chem. Commun. 1978, 604.
8. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
9. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
10. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
11. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
12. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
13. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
14. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
15. For reviews of metallocene-catalyzed alkene polymerization, see: (a) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (b) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (d) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (d) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205. (e) Resconi, L.; Cavallo, L.; Fait, A.; Pietmontesi, F. Chem. Rev. 2000, 100, 1253. (f) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391. (g) Rappe, A. K.; Skiff, W. M.; Casewitt, C. J. Chem. Rev. 2000, 100, 1435.
16. Casey, C. P.; Hallenbeck, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770.
17. (a) Casey, C. P.; Hallenbeck, S. L.; Wright, J. M.; Landis, C. R. J. Am. Chem. Soc. 1997, 119, 9680.
18. (b) Casey, C. P.; Fisher, J. J. Inorg. Chim. Acta 1998, 270, 5.
19. (c) Casey, C. P.; Fagan, M. A.; Hallenbeck, S. L. Organometallics 1998, 17, 287.
20. (d) Casey, C. P.; Fisher, J. J.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320.
21. For a preliminary communication, see: Casey, C. P.; Carpenetti, D. W., II; Sakurai, H. J. Am. Chem. Soc. 1999, 121, 9483.
22. Wu, Z.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867.
23. Galakhov, M. V.; Heinz, G.; Royo, P. Chem. Commun. 1998, 17.
24. Temme, B.; Karl, J.; Erker, G. Chem. Eur. J. 1996, 2, 919.
25. Inversion at the metal center has also been called site epimerization and back slipping.
26. (a) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 12021.
27. (b) Herzog, T. A.; Zubris, D. L.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 11988.
28. (c) Cavallo, L.; Guerra, G.; Vacatello, M.; Corrandini, P. Macromolecules 1991, 24, 1784.
29. (d) Busico, V.; Corrandini, P.; De Biasio, R.; Landriani, L.; Segre, A. L. Macromolecules 1994, 27, 4521.
30. (a) Ewen, J. A.; Jones, R. L.; Razavi, A.; Ferrara, J. D. J. Am. Chem. Soc. 1988, 110, 6255.
31. (b) Ewen, J. A. Makromol. Chem., Macromol. Symp. 1995, 89, 181.
32. Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1993, 115, 2083.
33. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245.
34. These compounds were synthesized by a procedure similar to that of: Tjaden, E. B.; Swenson, D. C.; Jordan, R. F.; Petersen, J. L. Organometallics 1995, 14, 371.
35. Reich, H. J. J. Chem. Educ. 1995, 72, 1086.
36. ‡ = 12 ± 1 eu for 8a to 8b.
37. 13C NMR spectra at these temperatures.
38. Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128.
39. s, was unsuccessful. We believe that 8a and 8b form, but are insoluble in toluene at low temperature, where only 11 is observed by NMR.
40. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
41. Chan, M. S. W.; Vanka, K.; Pye, C. C.; Ziegler, T. Organometallics 1999, 18, 4624.
42. 0 metal center is predicted to adopt a pyramidal geometry in order to accommodate an energetically favorable β-CH agostic interaction, (a) Ziegler, T.; Folga, E.; Berces, A. J. Am. Chem. Soc. 1993, 115, 636. (b) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (d) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (e) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
43. 0 metal center is predicted to adopt a pyramidal geometry in order to accommodate an energetically favorable β-CH agostic interaction, (a) Ziegler, T.; Folga, E.; Berces, A. J. Am. Chem. Soc. 1993, 115, 636. (b) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (d) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (e) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
44. 0 metal center is predicted to adopt a pyramidal geometry in order to accommodate an energetically favorable β-CH agostic interaction, (a) Ziegler, T.; Folga, E.; Berces, A. J. Am. Chem. Soc. 1993, 115, 636. (b) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (d) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (e) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
45. 0 metal center is predicted to adopt a pyramidal geometry in order to accommodate an energetically favorable β-CH agostic interaction, (a) Ziegler, T.; Folga, E.; Berces, A. J. Am. Chem. Soc. 1993, 115, 636. (b) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (d) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (e) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
46. 0 metal center is predicted to adopt a pyramidal geometry in order to accommodate an energetically favorable β-CH agostic interaction, (a) Ziegler, T.; Folga, E.; Berces, A. J. Am. Chem. Soc. 1993, 115, 636. (b) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (c) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (d) Weiss, H.; Ehrig, M.; Ahlrichs, R. J. Am. Chem. Soc. 1994, 116, 4919. (e) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
47. (a) Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
48. (b) Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1.
49. (c) Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85.
50. For a related yttrium system, we have measured the relative barriers of site epimerization and alkene insertion. Casey, C. P.; Lee, T.-Y.; Carpenetti, D. W., II. Manuscript in preparation.