Synthesis, characterization, isomerization, and reactivity of dimeric cyclopentadienylnickel amido complexes

Journal of the American Chemical Society

Volumn 118, Issue 5, 1996, Pages 1092-1104

  Holland, Patrick L ^a   Andersen, Richard A ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; NICKEL COMPLEX;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0029991308     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952882l     Document Type: Article

References (91)

1. For reviews on the subject, see: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163. (b) Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1.
2. For reviews on the subject, see: (a) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163. (b) Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1.
3. Mayer, J. M. Comments Inorg. Chem. 1988, 8, 125.
4. (a) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. Organometallics 1991, 10, 1875.
5. (b) Michelman, R. I. Ph.D. Thesis, University of California, Berkeley, 1993.
6. (a) Michelman, R. I.; Andersen, R. A.; Bergman, R. G. Organometallics 1993, 12, 2741.
7. (b) Michelman, R. I.; Ball, G. E.; Bergman, R. G.; Andersen, R. A. Organometallics 1994, 13, 869.
8. (a) Glueck, D. S.; Bergman, R. G. Organometallics 1991, 10, 1479.
9. (b) Glueck, D. S.; Winslow, L. J. N.; Bergman, R. G. Organometallics 1991, 10, 1462.
10. (c) Glueck, D. S.; Wu, J.; Hollander, F. W.; Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 2041.
11. (d) Dobbs, D. A.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 3836.
12. (a) Fryzuk, M. D.; MacNeil, P. A.; Rettig, S. J.; Secco, A. S.; Trotter, J. Organometallics 1982, 1, 918.
13. (b) Bartlett, R. A.; Chen, H.; Power, P. P. Angew. Chem. Int. Ed. Engl. 1989, 28, 316.
14. (c) Bradley, D. C.; Hursthouse, M. B.; Smallwood, R. J.; Welch, A. J. Chem. Commun. 1972, 872.
15. (d) Power, P. P. Comments Inorg. Chem. 1989, 8, 177 and references therein.
16. (e) Okeya, S.; Yoshimatsu, H.; Nakamura, Y.; Kawaguchi, S. Bull. Chem. Soc. Jpn. 1982, 55, 483.
17. (f) Tenten, A.; Jacobs, H. Z. Anorg. Allg. Chem. 1991, 604, 113.
18. (g) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921.
19. (h) Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750.
20. (i) Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371.
21. (j) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708.
22. (k) Hope, H.; Olmstead, M. M.; Murray, B. D.; Power, P. P. J. Am. Chem. Soc. 1985, 107, 712.
23. (l) Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148.
24. (m) Rahim, M.; Bushweller, C. H.; Ahmed, K. J. Organometallics 1994, 13, 4952.
25. See ref 1b and: (a) Kita, M.; Nonoyama, M. Polyhedron 1993, 12, 1027. (b) Alcock, N. W.; Bergamini, P.; Kemp, T. J.; Pringle, P. G. J. Chem. Soc., Chem. Commun. 1987, 235. (c) Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615.
26. See ref 1b and: (a) Kita, M.; Nonoyama, M. Polyhedron 1993, 12, 1027. (b) Alcock, N. W.; Bergamini, P.; Kemp, T. J.; Pringle, P. G. J. Chem. Soc., Chem. Commun. 1987, 235. (c) Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615.
27. See ref 1b and: (a) Kita, M.; Nonoyama, M. Polyhedron 1993, 12, 1027. (b) Alcock, N. W.; Bergamini, P.; Kemp, T. J.; Pringle, P. G. J. Chem. Soc., Chem. Commun. 1987, 235. (c) Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615.
28. (a) Matsunaga, P. T.; Hess, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 1994, 116, 3665.
29. (b) Pizzotti, M.; Cenini, S.; Porta, F.; Beck, W.; Erbe, J. J. Chem. Soc., Dalton Trans. 1978, 1155.
30. (c) Beck, W.; Bauder, M. Chem. Ber. 1970, 103, 583.
31. Villanueva, L. A.; Abboud, K.; Boncella, J. M. Organometallics 1991, 10, 2969.
32. Lee, S. W.; Trogler, W. C. Inorg. Chem. 1990, 29, 1099.
33. Bunel, E. E.; Valle, L.; Manriquez, J. M. Organometallics 1985, 4, 1680.
34. Smith, M. E.; Andersen, R. A. Submitted for publication.
35. For an extremely unstable nickel alkoxide complex, see: Baranwal, B. P.; Mehrotra, R. C. Aust. J. Chem. 1980, 33, 37.
36. No N-H stretching bands were observed in the IR spectra of 1 and 3, and only weak resonances appeared in the IR spectra of the other dimeric amides. These bands are often weak in metal amides, see: Chisholm, M. H.; Rothwell, I. P. In Comprehensive Coordination Chemistry: Wilkinson, G., Ed.; Pergamon: Oxford. 1987; Vol. 2, p 161.
37. Johnson, C. K., Report ORNL-3794, Oak Ridge National Laboratory, Oak Ridge, TN, 1965.
38. Smith, A. E. Inorg. Chem. 1972, 11, 165.
39. (a) López, G.; Garcia. G.; Ruiz, J.; Sánchez, G.; García. J.; Vicente, C. J. Chem. Soc., Chem. Commun. 1989, 1045.
40. (b) López. G.; Ruiz, J.; García, G.; Vicente, C.; Marti, J. M.; Hermoso, J. A.; Vegas, A.; Martínez-Ripoll, M. J. Chem. Soc., Dalton Trans. 1992, 53.
41. For a discussion of paramagnetic contributions to the chemical shift, see: Drago, R. S. Physical Methods for Chemists: Saunders College Publishing: Orlando, 1992; pp 232-243.
42. (a) Bax, A.; Griffey, R. H.; Hawkins, B. L. J. Magn. Reson. 1988, 55, 301.
43. (b) Evans, D. F. J. Chem. Soc. 1959, 2003.
44. (c) Baker, M. V.; Field, L. D.; Hambley, T. W. Inorg. Chem. 1988, 27, 2872.
45. (d) Jolly, W. L. The Synthesis and Characterization of Inorganic Compounds; Waveland: Prospect Heights. IL, 1970.
46. (a) Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615.
47. (b) Blake, R. E.; Heyn, R. H.; Tilley, T. D. Polyhedron 1992, 11, 709.
48. (a) Proulx, G.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 6382.
49. (b) Hanna, T. A.; Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 3292.
50. Marsella, J. A.; Folting, K.; Huffman, J. C.; Caulton, K. G. J. Am. Chem. Soc. 1981, 103, 5596.
51. -1.
52. (a) Bowen, R. E.; Gosling, K. J. Chem. Soc., Dalton Trans. 1974, 964.
53. (b) Wakatsuki, K.; Tanaka, T. Bull. Chem. Soc. Jpn. 1975, 48, 1475.
54. (c) Al-Wassil, A.-A. I.; Hitchcock, P. B.; Sarisaban, S.; Smith, J. D.; Wilson, C. L. J. Chem. Soc., Dalton Trans. 1985, 1929.
55. (d) Sauls, F. C.; Czekaj, C. L.; Interrante, L. V. Inorg. Chem. 1990, 29, 4688.
56. (e) Choquette, D. M.; Trimm, M. J.; Hobbs, J. L.; Rahim, M. M.; Ahmed, K. J.; Planalp, R. P. Organometallics 1992, 11, 529.
57. 2, and rationalized the predominance of the cis isomer on the basis of a transition-state argument involving cycloadditions. However, we were somewhat puzzled by this discussion, because near the end of ref 25b the authors make clear that the observed cis/trans ratios are thermodynamically controlled. See: (a) Beachley, O. T.; Tessier-Youngs, C. Inorg. Chem. 1979, 18, 3188.
58. (b) Beachley, O. T.; Bueno, C.; Churchill, M. R.; Hallock, R. B.; Simmons, R. G. Inorg. Chem. 1981, 20, 2423.
59. Brown, M. P.; Buckett, J.; Harding, M. M.; Lynden-Bell, R. M.; Mays, M. J.; Woulfe, K. W. J. Chem. Soc., Dalton Trans. 1991, 3097. They saw faster isomerization rates in polar solvents: this implicates a mechanism with solvent coordination, as in (c).
60. tAmyl)NiCp* was obtained in a roughly statistical ratio of products, as mentioned above. Cp*Ni(μ-NH(p-tol))(μ-NHxyl)NiCp* could be separated from 1 by crystallization, but we were unable to separate the two isomers of the mixed product from the two isomers of 3.
61. Mise, T.; Yamazaki, H. J. Organomet. Chem. 1979, 164, 391.
62. (a) Pasquali, M.; Gambarotta, S.; Floriani, C.; Villa, A. C.; Guastini, C. Inorg. Chem. 1981, 20, 165.
63. (b) Horlin, G.; Mahr, N.; Werner, H. Organometallics 1993, 12, 1993.
64. Crociani, B.; DiBianca, F.; Fontana, A.; Forsellini, E.; Bombieri, G. J. Chem. Soc., Dalton Trans. 1994, 407.
65. Yamamoto, T.; Sano, K.; Osakada, K.; Komiya, S.; Yamamoto, A.; Kushi, Y.; Tada, T. Organometallics 1990, 9, 2396.
66. Eisenberg, D. C.; Lawrie, C. J. C.; Moody, A. E.; Norton, J. R. J. Am. Chem. Soc. 1991, 113, 4888.
67. (a) Kolel-Veetil, M. K.; Ahmed, K. J. Inorg. Chem. 1994, 33, 4945.
68. (b) Kolel-Veetil, M. K.; Curley, J. F.; Yadav, P. R.; Ahmed, K. J. Polyhedron 1994, 13, 919.
69. (c) Kolel-Veetil, M. K.; Rheingold, A. L.; Ahmed, K. J. Organometallics 1993, 12, 3439.
70. (d) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 971.
71. (a) Andersen, R. A.; Blom, R.; Boncella, J. M.; Burns, C. J.; Volden, H. C. Acta Chem. Scand. 1987, A41, 24.
72. (b) Robbins, J. L.; Edelstein, N.; Spencer, B.; Smart, J. C. J. Am. Chem. Soc. 1982, 104, 1882.
73. Charles, R. G.; Pawlikowski, M. A. J. Phys. Chem. 1958, 62, 440.
74. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Materials: Pergamon: Oxford, 1980.
75. 1H} NMR spectrum.
76. (a) Otsuka, S.; Nakamura, A.; Tatsuno, Y. J. Am. Chem. Soc. 1969, 91, 6994.
77. (b) Nast, R.; Schulz, H.; Moerler, H.-D. Chem. Ber. 1970, 103, 777.
78. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2956.
79. Amman, C.; Meier, P.; Merbach, A. E. J. Magn. Reson. 1982, 46, 319.
80. Kaleidagraph v.2.1.3. Abelbeck Software, 1991.
81. Dobbs, D. A.; Bergman, R. G. Inorg. Chem. 1994, 33, 5329.
82. Reflections used for azimuthal scans were located near χ = 90° and the intensities were measured at 10° increments of rotation of the crystal about the diffraction vector.
83. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, England, 1974: Vol. IV.
84. (a) SMART Area-Detector Software Package; Siemens Industrial Automation, Inc.: Madison, WI, 1993.
85. (b) SAINT: SAX Area-Detector Integration Program; v. 4.024; Siemens Industrial Automation, Inc.: Madison, WI, 1995.
86. (c) XPREP (v.5.03): Part of the SHELXTL Crystal-Structure Determination Package; Siemens Industrial Automation: Madison, WI. 1994.
87. (d) TEXSAN: Crystal Structure Analysis Package; Molecular Structure Corporation, 1992.
88. (e) Hai-Fu, F. SAPI91: Structure Analysis Programs with Intelligent Control; Rigaku Corp.: Tokyo, 1991.
89. (f) Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla. C. DIRDIF92: The DIRDIF Program System; Technical Report of the Crystallography Laboratory, University of Nijmegen. The Netherlands, 1992.
90. (g) Creagh, D. C.; McAuley, W. J. International Tables for Crystallography: Kluwer Academic Publishers: Boston, 1992; Vol. C.
91. (h) Ibers, J. A.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781.