Stereoselective propene insertion reactions of rac-(EBI)Zr(η2-pyridyl)+ complexes

Organometallics

Volumn 16, Issue 25, 1997, Pages 5541-5555

  Dagorne, Samuel ^a   Rodewald, Stephan ^a   Jordan, Richard F ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000182134     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970750q     Document Type: Article

References (60)

1. For reviews concerning the chemistry of cationic group 4 metallocene complexes see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Ace. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
2. For reviews concerning the chemistry of cationic group 4 metallocene complexes see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Ace. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
3. For reviews concerning the chemistry of cationic group 4 metallocene complexes see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Ace. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
4. For reviews concerning the chemistry of cationic group 4 metallocene complexes see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Ace. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
5. For reviews concerning the chemistry of cationic group 4 metallocene complexes see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Ace. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
6. For reviews concerning the chemistry of cationic group 4 metallocene complexes see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Ace. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
7. (a) Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778.
8. (b) Jordan, R. F.; Taylor, D. F.; Baenziger, N. C. Organometallics 1990, 9, 1546.
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11. (e) Guram, A. S.; Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1991, 113, 1833.
12. (f) Guram, A. S.; Jordan, R. F. Organometallics 1991, 10, 3470.
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16. Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491.
17. For recent reviews concerning other applications of chiral zirconocene complexes, see: (a) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1263. (b) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Halterman, R. L. Chem. Rev. 1992, 92, 965.
18. For recent reviews concerning other applications of chiral zirconocene complexes, see: (a) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1263. (b) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Halterman, R. L. Chem. Rev. 1992, 92, 965.
19. For recent reviews concerning other applications of chiral zirconocene complexes, see: (a) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1263. (b) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Halterman, R. L. Chem. Rev. 1992, 92, 965.
20. HMQC: Bax, A.; Griffey, R. H.; Hawkins, B. L. J. Magn. Reson. 1983, 55, 301.
21. HMBC: Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093.
22. 3 in metallocene cation generation see: (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (b) Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128. (c) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114. (d) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451.
23. 3 in metallocene cation generation see: (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (b) Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128. (c) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114. (d) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451.
24. 3 in metallocene cation generation see: (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (b) Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128. (c) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114. (d) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451.
25. 3 in metallocene cation generation see: (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015. (b) Deck, P. A.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 6128. (c) Giardello, M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114. (d) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451.
26. 2): 2-methylpyridine, 2,5-dimethylpyridine: δ 8.55; pyridine, 3,5-dimethylpyridine: δ 8.50; 2-phenylpyridine, δ 8.70.
27. (a) Cahn, R. S.; Ingold, C. K.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
28. (b) Brunner, H. Top. Stereochem. 1989, 18, 129.
29. 3].
30. Bowen, D. E.; Rodewald, S. R.; Swenson, D. C.; Jordan, R. F., submitted for publication.
31. Micetich, R. G. In Pyridine and its Derivatives; Abramovich, R. A., Ed.; Wiley: New York, 1974; Vol. 2, p 305.
32. Silverstein, R. M.; Bassler, G. C.; Morril, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; p 15.
33. Similar pyridines have been reported. (a) Vernaudon, P.; Rajohrison, H. G.; Roussel, C. Bull. Soc. Chim. Fr. 1987, 1, 205. (b) Vymetal, J.; Koksochem, V. U.; Zavody, U.; Mezirici, V. Chem. Prum. 1979, 29, 354.
34. Similar pyridines have been reported. (a) Vernaudon, P.; Rajohrison, H. G.; Roussel, C. Bull. Soc. Chim. Fr. 1987, 1, 205. (b) Vymetal, J.; Koksochem, V. U.; Zavody, U.; Mezirici, V. Chem. Prum. 1979, 29, 354.
35. l are overlapped for 6d.
36. The propene reactions of the other pyridyl complexes were not investigated at low temperature because (i) 5c and 5f react slowly with propene at room temperature, making these systems inconvenient for low-temperature experiments, and (ii) the propene insertion reactions of 5b and 5d are >98% regio- and stereoselective at room temperature.
37. 2.
38. (a) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
39. (b) Rappé, A. K.; Colwell, K. S.; Casewit, C. J. Inorg. Chem. 1993, 32, 3438.
40. (a) Piemontesi, F.; Camurati, I.; Resconi, L., Balboni, D. Organometallics 1995, 14, 1256.
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42. (a) Wu, Z.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867.
43. (b) Strömberg, S.; Christopher, J. C.; Lee, C. W.; Swenson, D. C.; Jordan, R. F., manuscript in preparation.
44. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
45. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
46. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
47. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
48. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
49. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
50. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
51. For other d°-metal olefin complexes see: (a) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1585. (b) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8. (c) Casey, C. P.; Hallenback, S. L.; Pollock, D. W.; Landis, C. R. J. Am. Chem. Soc. 1995, 117, 9770. For computational studies see: (d) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252. (e) Lohrenz, J. C. W.; Woo, T. K.; Fan, L.; Ziegler, T. J. Organomet. Chem. 1995, 497, 91. (f) Yoshida, T.; Koga, N.; Morokuma, K. Organometallics 1995, 14, 746. (g) Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 2359. (h) Jensen, V. R.; Ystenes, M.; Wärnmark, K.; Åkermark, B.; Sevensson, M.; Siegbahn, P. E. M.; Bloomberg, M. R. A. Organometallics 1994, 13, 282.
52. Steric interactions and trends in the relative energies of the insertion transition states linking propene adducts 12/12′ and metallacycle products 6/6′ are probably similar to those in 12/12′.
53. vdw(H) = 1.0 Å. See: Bondi, A. J. Phys. Chem. 1964, 68, 441.
54. 6) = 2.61, 3.06 Å (modeled: 2.76, 3.14 Å), Zr-C-C-py dihedral angle -35.6 (modeled: -39.7°).
55. 2b
56. 3,11
57. 3) = 2.30.
58. Diamond, G. M.; Petersen, J. L.; Jordan, R. F. J. Am. Chem. Soc. 1996, 118, 8024.
59. BC = 49 Hz), 135.4, 125.7, 121.7.
60. -.