Application of amine elimination for the efficient preparation of electrophilic ansa-monocyclopentadienyl group 4 complexes containing an appended amido functionality. Structural characterization of [(C5H4)SiMe2(N-t-Bu)]ZrCl2(NMe 2H)

Organometallics

Volumn 15, Issue 6, 1996, Pages 1572-1581

  Carpenetti, Donald W ^a   Kloppenburg, Lioba ^a   Kupec, Justin T ^a   Petersen, Jeffrey L ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001445423     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950858a     Document Type: Article

References (80)

1. (a) Breslow, D. S.; Newburg, N. R. J. Am. Chem. Soc. 1957, 79, 5072.
2. (b) Natta, G.; Pino, P.; Mazzanti, G.; Giannini, U. J. Am. Chem. Soc. 1957, 79, 2976 and references cited therein.
3. Sinn, H.; Kaminsky, W. Adv. Organomet. Chem. 1980, 18, 99.
4. (a) Smith, J.; von Seyerl, J.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1979, 173, 175.
5. (b) Schnutenhaus, H.; Brintzinger, H. H. Angew. Chem., Int. Ed. Engl. 1979, 18, 777.
6. (c) Smith, J. A.; Brintzinger, H. H. J. Organomet. Chem. 1981, 218, 159.
7. (d) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233.
8. (e) Wild, F. R. W. P.; Wasiucionek, M.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1985, 288, 63.
9. (f) Wochner, F.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1985, 288, 69.
10. (g) Burger, P.; Hortmann, K.; Diebold, J.; Brintzinger, H. H. J. Organomet. Chem. 1991, 417, 9.
11. Achiral ansa-metallocenes: (a) Köpf, H.; Klouras, N. Z. Naturforsch., B 1983, 38, 321 and references cited therein, (b) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Makamura, A. Organometallics 1984, 3, 1470. (c) Kabi-Satpathy, A.; Bajgur, C. S.; Reddy, K. P.; Petersen, J. L. J. Organomet. Chem. 1989, 364, 105 and references cited therein. Chiral anscz-metallocenes: (d) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695. (e) Grossman, R. A.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501. (f) Halterman, R. L. Chem. Rev. 1992, 92, 965 and references cited therein.
12. Achiral ansa-metallocenes: (a) Köpf, H.; Klouras, N. Z. Naturforsch., B 1983, 38, 321 and references cited therein, (b) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Makamura, A. Organometallics 1984, 3, 1470. (c) Kabi-Satpathy, A.; Bajgur, C. S.; Reddy, K. P.; Petersen, J. L. J. Organomet. Chem. 1989, 364, 105 and references cited therein. Chiral anscz-metallocenes: (d) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695. (e) Grossman, R. A.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501. (f) Halterman, R. L. Chem. Rev. 1992, 92, 965 and references cited therein.
13. Achiral ansa-metallocenes: (a) Köpf, H.; Klouras, N. Z. Naturforsch., B 1983, 38, 321 and references cited therein, (b) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Makamura, A. Organometallics 1984, 3, 1470. (c) Kabi-Satpathy, A.; Bajgur, C. S.; Reddy, K. P.; Petersen, J. L. J. Organomet. Chem. 1989, 364, 105 and references cited therein. Chiral anscz-metallocenes: (d) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695. (e) Grossman, R. A.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501. (f) Halterman, R. L. Chem. Rev. 1992, 92, 965 and references cited therein.
14. Achiral ansa-metallocenes: (a) Köpf, H.; Klouras, N. Z. Naturforsch., B 1983, 38, 321 and references cited therein, (b) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Makamura, A. Organometallics 1984, 3, 1470. (c) Kabi-Satpathy, A.; Bajgur, C. S.; Reddy, K. P.; Petersen, J. L. J. Organomet. Chem. 1989, 364, 105 and references cited therein. Chiral anscz-metallocenes: (d) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695. (e) Grossman, R. A.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501. (f) Halterman, R. L. Chem. Rev. 1992, 92, 965 and references cited therein.
15. Achiral ansa-metallocenes: (a) Köpf, H.; Klouras, N. Z. Naturforsch., B 1983, 38, 321 and references cited therein, (b) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Makamura, A. Organometallics 1984, 3, 1470. (c) Kabi-Satpathy, A.; Bajgur, C. S.; Reddy, K. P.; Petersen, J. L. J. Organomet. Chem. 1989, 364, 105 and references cited therein. Chiral anscz-metallocenes: (d) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695. (e) Grossman, R. A.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501. (f) Halterman, R. L. Chem. Rev. 1992, 92, 965 and references cited therein.
16. Achiral ansa-metallocenes: (a) Köpf, H.; Klouras, N. Z. Naturforsch., B 1983, 38, 321 and references cited therein, (b) Yasuda, H.; Nagasuna, K.; Akita, M.; Lee, K.; Makamura, A. Organometallics 1984, 3, 1470. (c) Kabi-Satpathy, A.; Bajgur, C. S.; Reddy, K. P.; Petersen, J. L. J. Organomet. Chem. 1989, 364, 105 and references cited therein. Chiral anscz-metallocenes: (d) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695. (e) Grossman, R. A.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501. (f) Halterman, R. L. Chem. Rev. 1992, 92, 965 and references cited therein.
17. (a) Ewen, J. A. J. Am. Chem. Soc. 1984, 106, 6355.
18. (b) Ewen, J. A.; Haspeslagh, L.; Atwood, J. L.; Zhang, H. J. Am. Chem. Soc. 1987, 109, 6544.
19. (c) Ewen, J. A.; Haspeslagh, L.; Elder, M. J.; Atwood, J. L.; Zhang, H.; Cheng, H. In Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W., Sinn, H., Eds.; Springer-Verlag: Berlin, 1988; p 281.
20. (d) Kaminsky, W.; Külper, K.; Brintzinger, H. H.; Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507.
21. (e) Kaminsky, W.; Engehausen, R.; Zoumis, K.; Spaleck, W.; Rohrmann, J. Makromol. Chem. 1992, 193, 1643.
22. (f) Spaleck, W.; Antberg, M.; Rohrmann, J.; Winter, A.; Bachmann, B.; Kiprof, P.; Behm, J.; Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 1347.
23. (g) Hortmann, K.; Brintzinger, H. H. New J. Chem. 1992, 16, 51.
24. (h) Spaleck, W.; Küber, F.; Winter, A.; Rohrmann, J.; Bachmann, B.; Antberg, M.; Dolle, V.; Paulus, E. F. Organometallics 1994, 13, 954.
25. (i) Stehling, U.; Diebold, J.; Kirsten, R.; Röll, W.; Brintzinger, H. H.; Jüngling, S.; Mülhaupt, R.; Langhauser, F. Organometallics 1994, 13, 964.
26. (a) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6270.
27. (b) Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91.
28. (a) Jordan, R. F.; Bradley, P. K.; LaPointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
29. (b) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325 and references cited therein.
30. (c) Jia, L.; Yang, X.; Ishihara, A.; Marks, T. J. Organometallics 1995, 14, 3135 and references cited therein.
31. (a) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623.
32. (b) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 2, 74.
33. (c) Shapiro, P. J.; Bunel, E. E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867.
34. (a) Canich, J. M. Eur. Patent Appl. EP-420-436-A1, 1991.
35. (b) Canich, J. M. U.S. Patent Appl. 5,026,798, 1991.
36. (c) Canich, J. M.; Hlatky, G. G.; Turner, H. W. PCT Appl. W092-00333, 1992.
37. Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Eur. Patent Appl. EP-416-815-A2, 1991.
38. 2.
39. (a) Okuda, J. Chem. Ber. 1990, 123, 1649.
40. (b) Okuda, J.; Schattenmann, F. J.; Wocaldo, S.; Massa, W. Organometallics 1995, 14, 789.
41. 2, q, 118).
42. 2, q, 119).
43. 3].• Lubben, T. V.; Wolczanski, P. T.; Van Duyne, G. D. Organometallics 1984, 3, 977.
44. 2)]: Bazan, G. C.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1993, 12, 2126.
45. 2]: Quan, R. W.; Bazan, G. C.; Kiely, A. F.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4489.
46. 2]: Bazan, G. C.; Rodriquez, G.; Cleary, B. P. J. Am. Chem. Soc. 1994, 116, 2177.
47. (a) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
48. (b) Lappert, M. F.; Power, P. B.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amines; Ellis Horwood: Chichester, West Sussex, U.K., 1980.
49. Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936.
50. Herrmann, W. A.; Morawietz, M. J. A. J. Organomet. Chem. 1994, 482, 169.
51. Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
52. Gordon, A. J.; Ford, R. A. The Chemist's Companion; Wiley-Interscience: New York, 1972.
53. Setukowski, D. G.; Stucky, G. D. Inorg. Chem. 1975, 14, 2192.
54. Manzer, L. E. Inorg. Synth. 1982, 21, 134.
55. Fendrick, C. M.; Schertz, L. D.; Day, V. W.; Marks, T. J. Organometallics 1988, 7, 1828.
56. (a) Bradley, D. C.; Thomas, I. M. Proc. Chem. Soc., London 1959, 225.
57. (b) Bradley, D. C.; Thomas, I. M. Proc. Chem. Soc., London 1960, 3857.
58. (c) Chisholm, M. H.; Hammond, C. E.; Huffman, J. C. Polyhedron 1988, 7, 2515.
59. XSCANS (version 2.0) is a diffractometer control system developed by Siemens Analytical X-ray Instruments, Madison, WI.
60. SHELXL-93 is a FORTRAN-77 program (Professor G. Sheldrick, Institut für Anorganische Chemie, University of Göttingen, ". D-37077 Göttingen, Germany) for single-crystal X-ray structural analyses.
61. 2) on 16 non-hydrogen atoms and 19 idealized hydrogen atoms converged with R1 = 0.0415 for 2052 data with I > Zσ(I) and GOF = 1.078.
62. Davis, J. H.; Sun, H.; Redfield, D.; Stucky, G. D. J. Magn. Reson. 1980, 37, 441.
63. 3Si-NHMe. See: Walsh, R. Acc. Chem. Res. 1981, 14, 246.
64. Pupi, R. M.; Coalter, J. N.; Petersen, J. L. J. Organomet. Chem. 1996, 497, 17.
65. Giolando, D. M.; Kirschbaum, K; Graves, L. J.; Bolle, U. Inorg. Chem. 1992, 31, 3887.
66. Bai, Y.; Roesky, H. W.; Noltemeyer, M. Z. Z. Anorg. Allg. Chem. 1991, 595, 21.
67. 2) on 20 non-hydrogen atoms and 27 idealized hydrogen atoms converged with R1 = 0.0307 for 3886 data with I > 2σ(I) and GOF = 1.026.
68. Martin, A.; Mena, M.; Yelamos, C.; Serrano, R.; Raithby, P. R. J. Organomet. Chem. 1994, 467, 79.
69. 2) on 17 independent non-hydrogen atoms and 23 idealized hydrogen atoms converged with R1 = 0.0299 for 2849 data with I > 2σ(I) and GOF = 1.029.
70. du Plooy, K. E.; Moll, U.; Wocaldo, S.; Massa, W.; Okuda, J. Organometallics 1995, 14, 3129.
71. Airoldi, C.; Bradley, D. C.; Chudzynska, H.; Hursthouse, M. B.; Abdul Malik, K. M.; Raithby, P. R. J. Chem. Soc., Dalton Trans. 1980, 2010.
72. Hagen, K.; Holwill, C. J.; Rice, D. A.; Runnacles, J. D. Inorg. Chem. 1988, 27, 2032.
73. Nugent, W. A.; Harlow, R. L. Inorg. Chem. 1979, 18, 2030.
74. Diamond, G. M.; Petersen, J. L.; Jordan, R. F., unpublished results.
75. Bradley, D. C.; Chudzynska, H.; Backer-Dirks, J. D. J.; Hurst-house, M. B.; Ibrahim, A. A.; Montevalli, M.; Sullivan, A. C. Polyhedron 1990, 9, 1423.
76. Black, D. G.; Swenson, D. C.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3539.
77. (a) Prout, K.; Cameron, T. S.; Forder, R. A.; Critchley, S. R.; Denton, B.; Rees, G. V. Acta Crystallogr., Sect. B 1970, B30, 2290.
78. (b) Jeffrey, J.; Lappert, M. F.; Luong-Thi, N. T.; Webb, M.; Atwood, J. L.; Hunter, W. E. J. Chem. Soc., Dalton Trans. 1981, 1953 and references cited therein.
79. (c) Bajgur, C. S.; Tikkanen, W. R.; Petersen, J. L. Inorg. Chem. 1985, 24, 2539 and references cited therein.
80. (d) Rogers, R. D.; Benning, M. M.; Kurihara, L. K.; Moriarty, K. J.; Rausch, M. D. J. Organomet. Chem. 1985, 293, 51.