Trapping of acetylene by a zirconocene terminal imido complex

Organometallics

Volumn 19, Issue 12, 2000, Pages 2365-2372

  Harlan, C Jeff ^a   Tunge, Jon A ^a   Bridgewater, Brian M ^a   Norton, Jack R ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CARBON; CRYSTAL STRUCTURE; HEATING; HYDROGEN BONDS; NITROGEN; REACTION KINETICS; X RAY CRYSTALLOGRAPHY; ZIRCONIUM;

LEWIS BASE; ZIRCONOCENE TERMINAL IMIDO COMPLEX;

ORGANOMETALLICS;

EID: 0033701147     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000165g     Document Type: Article

References (73)

1. (a) Meyer, K. E.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 974-985.
2. (b) Krska, S. W.; Zuckerman, R. L.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 11828-11829.
3. (c) Zuckerman, R. L.; Krska, S. W.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 751-761.
4. (a) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719.
5. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763.
6. Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 664-665. Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 3389-3391.
7. Hill, J. E.; Profilet, R. D.; Fanwick, P. E.; Rothwell, I. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 664-665. Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 3389-3391.
8. (a) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324.
9. (b) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459-5460.
10. (c) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489.
11. (d) Fairfax, D.; Stein, M.; Livinghouse, T.; Jensen, M. Organometallics 1997, 16, 1523-1525.
12. (a) Mountford, P.; Nikonov, G. I.; Swallow D. J. Chem. Soc., Chem. Commun. 1996, 1835-1836.
13. (b) Blake, A. J.; McInnes, J. M.; Mountford, P.; Nikonov, G. I.; Swallow, D.; Watkin, D. J. J. Chem. Soc., Dalton Trans. 1999, 379-391.
14. (c) Thorman, J. L.; Guzei, I. A.; Young, V. G., Jr.; Woo, L. K. Inorg. Chem. 1999, 38, 3814-3824.
15. (a) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 8729-8731.
16. (b) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723.
17. (a) Bennett, J. L.; Wolczanski, P. T. J. Am. Chem. Soc. 1997, 119, 10696-10719.
18. (b) Schaller, C. P.; Cummins, C. C.; Wolczanski, P. T. J. Am. Chem. Soc. 1996, 118, 591-611.
19. (c) Cummins, C. C.; Baxter, S. M.; Wolczanski, P. T. J. Am. Chem. Soc. 1988, 110, 8731-8733.
20. (d) Schaller, C. P.; Bonanno, J. B.; Wolczanski, P. T. J. Am. Chem. Soc. 1994, 116, 4133-4134.
21. (e) Bennett, J. L.; Wolczanski, P. T. J. Am. Chem. Soc. 1994, 116, 2179-2180.
22. Bashall, A.; Collier, P. E.; Gade, L. H.; McPartlin, M.; Mountford, P.; Trösch, D. J. M. J. Chem. Soc., Chem. Commun. 1998, 2555-2556.
23. (a) Harlan, C. J.; Hascall, T.; Fujita, E.;. Norton, J. R. J. Am. Chem. Soc. 1999, 121, 7274-7275.
24. (b) Harlan, C. J.; Bridgewater, B. M.; Hascall, T.; Norton, J. Organometallics 1999, 18, 3827-3834.
25. Lee, S. Y.; Bergman, R. G. Tetrahedron 1995, 51, 4255-4276.
26. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 4543. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 7825-7834.
27. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 4543. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 7825-7834.
28. Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405-13414.
29. Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 5393-5394.
30. 0 group 5 complexes. (a) Blake, R. E., Jr.; Antonelli, D. M.; Henling, L. M.; Schaefer, W. P.; Hardcastle, K. I.; Bercaw, J. E. Organometallics 1998, 17, 718-725. (b) de With, J.; Horton, A. D.; Orpen, A. G. Organometallics 1993, 12, 1493-1496. (c) de With, J.; Horton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 903-905.
31. 0 group 5 complexes. (a) Blake, R. E., Jr.; Antonelli, D. M.; Henling, L. M.; Schaefer, W. P.; Hardcastle, K. I.; Bercaw, J. E. Organometallics 1998, 17, 718-725. (b) de With, J.; Horton, A. D.; Orpen, A. G. Organometallics 1993, 12, 1493-1496. (c) de With, J.; Horton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 903-905.
32. 0 group 5 complexes. (a) Blake, R. E., Jr.; Antonelli, D. M.; Henling, L. M.; Schaefer, W. P.; Hardcastle, K. I.; Bercaw, J. E. Organometallics 1998, 17, 718-725. (b) de With, J.; Horton, A. D.; Orpen, A. G. Organometallics 1993, 12, 1493-1496. (c) de With, J.; Horton, A. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 903-905.
33. 6
34. 1H NMR).
35. Thorn, D. L.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1981, 103, 357-363.
36. (a) Nugent, W. A.; Harlow, R. L. Inorg. Chem. 1979, 18, 2030-2032.
37. (b) Arney, D. J.; Bruck, M. A.; Huber, S. R.; Wigley, D. E. Inorg. Chem. 1992, 31, 3749-3755.
38. (a) Stella, S.; Chiang, M.; Floriani, C. J. Chem. Soc., Chem Commun. 1987, 161-163.
39. (b) Crowther, D. J.; Baenziger, N. C.; Jordan, R. F. J. Am. Chem. Soc. 1991, 113, 1455-1457.
40. Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16-20.
41. Smith, G. M.; Sabat, M.; Marks, T. J. J. Am. Chem. Soc. 1987, 109, 1854-1856.
42. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; Part A: Structure and Mechanisms, 3rd ed.; Plenum Press: New York, 1990.
43. (a) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764.
44. (b) Subramanian, R.; Koch, S. A.; Harbison, G. S. J. Phys. Chem. 1993, 97, 8625-8629.
45. Hartner, F. W., Jr.; Schwartz, J.; Clift, S. M. J. Am. Chem. Soc. 1983, 105, 640-641.
46. Van De Heisteeg, B. J. J.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. J. Organomet. Chem. 1986, 308, 1-10.
47. Hartner, F. W., Jr.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4979-4981.
48. 13C NMR resonances are in the range δ 178-154. (a) Inamoto, N.; Kushida, K.; Masuda, S.; Ohta, H.; Satoh, S.; Tamura, Y.; Tokumaru, K.; Tori, K.; Yoshida, M. Tetrahedron Lett. 1974, 3617-3620. (b) Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451-458. (c) Fraser, R. R.; Chuaqui-Offermanns, N. Can. J. Chem. 1981, 59, 3007-3011. (d) Klusener, P. A. A.; Tip, L.; Brandsma, L. Tetrahedron 1991, 47, 2041-2064.
49. 13C NMR resonances are in the range δ 178-154. (a) Inamoto, N.; Kushida, K.; Masuda, S.; Ohta, H.; Satoh, S.; Tamura, Y.; Tokumaru, K.; Tori, K.; Yoshida, M. Tetrahedron Lett. 1974, 3617-3620. (b) Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451-458. (c) Fraser, R. R.; Chuaqui-Offermanns, N. Can. J. Chem. 1981, 59, 3007-3011. (d) Klusener, P. A. A.; Tip, L.; Brandsma, L. Tetrahedron 1991, 47, 2041-2064.
50. 13C NMR resonances are in the range δ 178-154. (a) Inamoto, N.; Kushida, K.; Masuda, S.; Ohta, H.; Satoh, S.; Tamura, Y.; Tokumaru, K.; Tori, K.; Yoshida, M. Tetrahedron Lett. 1974, 3617-3620. (b) Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451-458. (c) Fraser, R. R.; Chuaqui-Offermanns, N. Can. J. Chem. 1981, 59, 3007-3011. (d) Klusener, P. A. A.; Tip, L.; Brandsma, L. Tetrahedron 1991, 47, 2041-2064.
51. 13C NMR resonances are in the range δ 178-154. (a) Inamoto, N.; Kushida, K.; Masuda, S.; Ohta, H.; Satoh, S.; Tamura, Y.; Tokumaru, K.; Tori, K.; Yoshida, M. Tetrahedron Lett. 1974, 3617-3620. (b) Allen, M.; Roberts, J. D. Can. J. Chem. 1981, 59, 451-458. (c) Fraser, R. R.; Chuaqui-Offermanns, N. Can. J. Chem. 1981, 59, 3007-3011. (d) Klusener, P. A. A.; Tip, L.; Brandsma, L. Tetrahedron 1991, 47, 2041-2064.
52. 8 small amounts of complexes 1-THF and 4a are observed.
53. (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Angermund, K.; Krüger, C. Organometallics 1989, 8, 911-920.
54. (b) Ahlers, W.; Temme, B.; Erker, G.; Fox, T. J. Organomet. Chem. 1997, 527, 191-201.
55. (c) Hou, Z.; Breen, T. L.; Stephan, D. W. Organometallics 1993, 12, 3158-3167.
56. (d) Varga, V.; Hiller, J.; Thewalt, U.; Polásek, M.; Mach, K. J. Organomet. Chem. 1998, 553, 15-22.
57. (e) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. J. Organomet. Chem. 1992, 428, 13-47.
58. Erker, G.; Frömberg, W.; Mynott, R.; Gabor, B.; Krüger, C. Angew. Chem., Int Ed. Engl. 1986, 25, 463-465.
59. For examples in titanocene chemistry see: Lang, H.; Blau, S.; Nuber, B.; Zsolnai, L. Organonetallics 1995, 14, 3216-3223, and references therein.
60. Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466-8477.
61. Binger, P.; Müller, P.; Herrmann, A. T.; Philipps, P.; Gabor, B.; Langhauser, F.; Krüger, C. Chem. Ber. 1991, 124, 2165-2170.
62. Bai, Y.; Roesky, H. W.; Noltemeyer, M.; Witt, M. Chem. Ber. 1992, 125, 825-831.
63. (a) Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715.
64. (b) King, W. A.; Di Bella, S.; Gulino, A.; Lanza, G.; Fragala, I. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 355-366.
65. (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737-738.
66. (b) Han. C. C.; Katz, T. J. Organometallics 1985, 4, 2186-2195.
67. (c) Schrock, R. R.; Luo, S.; Lee, J. C., Jr.; Zanetti, N. C.; Davis, W. M. J. Am. Chem. Soc. 1996, 118, 3883-3895.
68. (d) Wallace, K. C.; Liu, A. H.; Davis, W. M.; Schrock, R. R. Organometallics 1989, 8, 644-654.
69. (e) Doxsee, K. M.; Juliette, J. J. J.; Mouger, J. K. M.; Zientara, K. Organometallics 1993, 12, 4742-4744.
70. 1-vinyl carbene structure. Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chen., Int. Ed. Engl. 1989, 28, 610-611.
71. 1H NMR.
72. Because the equilibrium between 3b and 4b/1b already favors 3b, addition of 1b will not result in a significant change in the concentration of 3b. Thus the direct conversion of 3b to 5b cannot be accelerated by added 1b.
73. Sheldrick, G. M. SHELXTL, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data; University of Göttingen, Göttingen, Federal Republic of Germany, 1981.