Synthesis of group 4 metal rac-(EBI)M(NR2)2 complexes by amine elimination. Scope and limitations

Organometallics

Volumn 15, Issue 19, 1996, Pages 4030-4037

  Diamond, Gary M ^a   Jordan, Richard F ^a   Petersen, Jeffrey L ^b  

^a E11 SSH   (United States)

^b WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001466510     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960103j     Document Type: Article

References (88)

1. (a) Thayer, A. M. Chem. Eng. News 1995, 73 (37), 15.
2. (b) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
3. (c) Sinclair, K. B.; Wilson, R. B. Chem. Ind. 1994, 857.
4. (d) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
5. (e) Horton, A. D. Trends Polym. Sci . 1994, 2, 158.
6. (f) Farina, M. Trends Polym. Sci . 1994, 2, 80.
7. (g) Bochmann, M. Nachr. Chem. Tech. Lab. 1993, 41, 1220.
8. (h) Kaminsky, W.; Engehausen, R.; Zoumis, K.; Spaleck, W.; Rohrmann, J. Makromol. Chem. 1992, 193, 1643.
9. (i) Marks, T. J. Acc. Chem. Res. 1992, 25, 57.
10. (j) Jordan, R. F. Adv. Organometallic Chem. 1991, 32, 325.
11. (k) Spaleck, W.; Antberg, M.: Dolle, V.; Klein, R.; Rohrmann, J.; Winter, A. New J. Chem. 1990, 14, 499.
12. (l) Kaminsky, W.; Kulper, K.; Brintzinger, H. H.; Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24. 507.
13. (m) Ewen, J. A. J. Am. Chem. Soc. 1984, 106, 6355.
14. Leading reference: Halterman, R. L. Chem. Rev. 1992, 92, 965.
15. (a) Kaminsky, W.; Rabe, O.; Schauwienold, A. M.; Schupfner, G. U.; Hanss, J.; Kopf, J. J. Organomet. Chem. 1995, 497, 181.
16. (b) Stehling, U.; Diebold, J.; Kirsten, R.; Roll, W.; Brintzinger, H. H.; Jungling, S.; Mülhaupt, R.; Langhauser, F. Organometallics 1994, 13, 964.
17. (c) Spaleck, W.; Kuber, F.: Winter, A.; Rohrmann, J.; Bachmann, B.; Antberg, M.; Dolle, V.: Paulus, E. F. Organometallics 1994, 13, 954.
18. (d) 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.
19. (e) Erickson, M. S.; Fronczek, F. R.; McLaughlin, M. L. J. Organomet. Chem. 1991, 415, 75.
20. (a) Chacon, S. T.; Coughlin, E. B.; Henling, L. M.; Bercaw, J. E. J. Organomet. Chem. 1995, 497, 171.
21. (b) Collins, S.; Hong, Y.; Ramachandran, R.: Taylor, N. J. Organometallics 1991, 10, 2349.
22. (c) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695.
23. (d) Wiesenfeldt, H.: Reinmuth. A.; Barsties, E.; Evertz, K.; Brintzinger, H. H. J. Organomet. Chem. 1989, 369, 359.
24. (e) Mise, T.; Miya, S.; Yamazaki, H. Chem. Lett. 1989, 1853.
25. (a)Broene, R. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 12569.
26. (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1992, 33, 1005.
27. (c) Halterman, R. L.; Ramsey, T. M. Organometallics 1993, 12, 2879.
28. (d) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732.
29. (e) Chen, Z.; Halterman, R. L. J. Am. Chem. Soc. 1992, 114, 2276.
30. (f) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
31. (g) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703.
32. (h) Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
33. (i) Odenkirk, W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1995, 1181.
34. (j) Jaquith, J. B.; Gaun, J.; Wang, S.; Collins, S. Organometallics: 1995, 14, 1079.
35. (k) Kuntz, B. A.; Ramachandran, R.; Taylor, N. J.; Guan, J.; Collins, S. J. Organomet. Chem. 1995, 497, 133.
36. (l) Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642.
37. (m) Carter, M. B.; Schiott, B.; Guiterrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667.
38. Wild, F. R. W. P.; Zsolnai. L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233.
39. Collins, S.; Kuntz, B. A.; Taylor, N. J.; Ward, D. G. J. Organomet. Chem. 1988, 342, 21.
40. See footnote 7 in: Collins, S.; Kuntz, B. A.; Hong, Y. ,J. Org. Chem. 1989, 54, 4154.
41. Ewen, J. A.; Haspeslagh, L.; Atwood, J. L.; Zhang, H. J. Am. Chem. Soc. 1987, 109, 6544.
42. Ewen, J. A.; Haspeslagh, L.; Elder, M. J.; Atwood, J. L.; Zhang, H.; Cheng, H. N. In Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky W., Sinn H., Eds; Springer-Verlag: Berlin, 1988; p 281.
43. (a) Grossman, R. B.; Doyle, R. A.; Buchwald, S. L. Organometallics 1991, 10, 1501.
44. (b) Buchwald, S. L.; Grossman, R. B. U.S. Patent 5 004 820, 1991.
45. (a) Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
46. (b) Diamond, G. M.; Jordan, R. F.; Petersen, J. L., J. Am. Chem. Soc., in press.
47. Kim, I.; Jordan, R. F. Macromolecules 1996, 29, 489.
48. Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4045.
49. Christopher, J. N.; Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4038.
50. Ross, K. J.; Swenson, D. C.; Jordan, R. F.; Rogers, R. D. Manuscript in preparation.
51. Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, U.K., 1980.
52. Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
53. (a) Bradley, D. C.; Thomas, I. M. Proc. Chem. Soc. 1959, 225.
54. (b) Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1960, 3857.
55. (c) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259.
56. Piemontesi, F.; Camurati, I.; Resconi, L.; Balboni, D.; Sironi, A.; Moret, M.; Ziegler, R.; Piccolrovazzi, N. Organometallics 1995, 14, 1256.
57. 3).
58. 2 ligands. See: Nugent, W. A.; Ovenall, D. W.; Holmes, S. J. Organometallics 1983, 2, 161.
59. Black, D. G.; Swenson, D. C.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3539.
60. 2H, 84 °C.
61. 2H. Grimm, D. T.; Bartmess, J. E. J. Am. Chem. Soc. 1992, 114, 1227.
62. 12 the N-C bond lengths are very similar in both complexes (1.45-1.48 Å).
63. 2 as an orange crystalline solid in 43% isloated yield.
64. Shannon, R. D. Acta Crystallogr., Sect. A 1976, 32, 751.
65. (a) Haaland, A.; Rypdal, K.; Volden, H. V.; Andersen, R. A. J. Chem. Soc., Dalton Trans. 1992, 891.
66. (b) Martin, A.; Mena, M.; Yelamos, C.; Serrano, R.; Raithby, P. R. J. Organomet. Chem. 1994, 467, 79.
67. (c) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311.
68. (a) Sartain, W. J.; Huffman, J. C.; Lundquist. E. G.; Streib, W. G.; Caulton, K. G. J. Mol. Catal. 1989, 56, 20.
69. (b) Chisholm, M. H.; Hammond, C. E.; Huffman, J. C. Polyhedron 1988, 7, 2515.
70. (c) Hagen, K.; Holwill, C. J.; Rice, D. A.; Runnacles, J. D. Inorg. Chem. 1988, 27, 2032.
71. An alternative strategy would involve the use of primary amide Ti starting materials. However, such compounds are neither readily accessible nor stable. Nielson, A. J. Inorg. Chim. Acta 1988, 154, 177.
72. Smith, J. A.; Von Seyerl, J.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1979, 173, 175.
73. Shaltout, R. M.; Corey, J. Y.; Rath, N. P. J. Organomet. Chem. 1995, 503, 205.
74. Clearfield, A.; Warner, D. K.; Saldarriaga-Molina, C. H.; Ropal, R.; Bernal. I. Can. J. Chem. 1975, 53, 1622.
75. 2).
76. 2).
77. 3).
78. (a) Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701.
79. (b) Ziegler, T.; Tschinke, V.; Versluis, L.; Baerends, E. V.; Ravenek, W. Polyhedron 1988, 7, 1625.
80. (c) Cardin, D. J.; Lappert, M. F.; Raston, C. L. Chemistry of Organo-zirconium and -hafnium Compounds; Ellis Horwood: Chichester, West Sussex, U. K., 1986; p 16.
81. (d) Lappert, M. F.; Patil, D. S.; Pedley, J. B. J. Chem. Soc., Chem. Commun. 1975, 830.
82. Brintzinger, H. H. In Transition Metals and Organometallics as Catalysts for Olefin Polymerization; Kaminsky, W., Sinn, H., Eds.; Springer-Verlag: Berlin, 1988; p 249.
83. 2Hf(H)(NHMe), 2.03 Å: Hillhouse, G. L.; Bulls, A. R.; Santarsiero, B. D.; Bercaw, J. E. Organometallics 1988, 7, 1309.
84. 2, 2.09 Å: Black, D. G.; Jordan, R. F.; Rogers, R. D. Manuscript in preparation,
85. 2, 2.12 Å average: Zambrano, C. H.; Profilet, R. D.; Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Polyhedron 1993, 12, 689.
86. Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
87. SHELXL-93 is a FORTRAN-77 program (Professor G. Sheldrick, Institut fur Anorganische Chemie, University of Gottingen, D-37077 Gottingen, Germany) for single-crystal X-ray structural analyses.
88. 1/2, where n is the number of reflections and p is the number of parameters varied during the last refinement cycle.