Synthesis and structures of cationic aluminum and gallium amidinate complexes

Journal of the American Chemical Society

Volumn 122, Issue 2, 2000, Pages 274-289

  Dagorne, Samuel ^a   Guzei, Ilia A ^b   Coles, Martyn P ^a   Jordan, Richard F ^a,c  

^a UNIVERSITY OF IOWA   (United States)

^b IOWA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; GALLIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033985161     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992104j     Document Type: Article

References (91)

1. (a) Starowieyski, K. B. In Chemistry of Aluminium, Gailium, Indium and Thallium, Downs, A. J., Ed.; Chapman & Hall: London, UK, 1993; pp 322-371.
2. (b) Eisch, J. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, UK, 1995; Vol. 11, Chapter 6.
3. (c) Matyjaszewski, K., Ed. Cationic Polymerizations: Mechanisms, Synthesis and Applications; Marcel Dekker: New York, 1996.
4. (d) Kennedy, J. P.; Marechal, E. Carbocationic Polymerization; Wiley-Interscience: New York, 1982.
5. (e) Eisch, J. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, UK, 1995; Vol. 1, Chapter 10.
6. (a) Ziegler, K., Gellert, H. G. Justus Liebigs Ann. Chem. 1950, 567, 195.
7. (b) Skinner, W. A.; Bishop, E.; Cambour, P.; Fuqua, S.; Lim, P. Ind. Eng. Chem. 1960, 52, 695.
8. (c) Skupínska, J. Chem. Rev. 1991, 91, 613.
9. (d) Al-Jarallah, A. M.; Anabtawi, J. A.; Siddiqui, M. A. B.; Aitani, A. M.; Al-Sa'doun, A. W. Catal. Today 1992, 14, 42.
10. (a) Bochmann, M.; Dawson, D. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2226.
11. (b) Atwood, D. A.; Jegier, J. A.; Rutherford, D. J. Am. Chem. Soc. 1995, 117, 6779.
12. (c) Jegier, J. A.; Atwood, D. A. Inorg. Chem. 1997, 36, 2034.
13. (d) Emig, N.; Nguyen, H.; Krautscheid, H.; Reau, R.; Cazaux, J. B.; Bertrand, G. Organometallics 1998, 17, 3599.
14. (e) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502.
15. (f) For a review, see: Atwood, D. A. Coord. Chem. Rev. 1998, 176, 407.
16. (a) Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
17. (b) Ihara, E.; Young, V. G., Jr.; Jordan, R. F. J. Am. Chem. Soc. 1998, 120, 8277.
18. (c) Bruce, M.; Gibson, V. C.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 2523.
19. Bochmann, M.; Sarsfield, M. J. Organometallics 1998, 17, 5908.
20. (a) Strauss, S. H. Chem. Rev. 1993, 93, 927.
21. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255.
22. (c) Turner, H. W. Eur. Pat. Appl. 0 277 004, 1988.
23. (a) Radzewich, C. E.; Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1998, 120, 9384.
24. (b) Radzewich, C. E.; Guzei, I. A.; Jordan, R. F. J. Am. Chem. Soc. 1999, 121, 8673.
25. (c) Radzewich, C. E.; Jordan, R. F. Manuscript in preparation.
26. 4] (toluene, 100°C, 6 atm ethylene); activity = 1375 g PE/(mol·h·atm).
27. (a) Edelmann, F. T. Coord. Chem. Rev. 1994, 137, 403.
28. (b) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219.
29. 4] (toluene, 100°C, 6 atm ethylene); activity = 2708 g PE/(mol·h·atm).
30. Ga = 1.8.
31. + fragment. (a) Shriver, D. F.; Parry, R. W. Inorg. Chem. 1962, 1, 835. (b) Tobias, R. S.; Sprague, M. J.; Glass, G. E. Inorg. Chem. 1968, 7, 1714. (c) Olapinsky, H.; Weidlein, J. J. Organomet. Chem. 1973, 54, 87.
32. + fragment. (a) Shriver, D. F.; Parry, R. W. Inorg. Chem. 1962, 1, 835. (b) Tobias, R. S.; Sprague, M. J.; Glass, G. E. Inorg. Chem. 1968, 7, 1714. (c) Olapinsky, H.; Weidlein, J. J. Organomet. Chem. 1973, 54, 87.
33. + fragment. (a) Shriver, D. F.; Parry, R. W. Inorg. Chem. 1962, 1, 835. (b) Tobias, R. S.; Sprague, M. J.; Glass, G. E. Inorg. Chem. 1968, 7, 1714. (c) Olapinsky, H.; Weidlein, J. J. Organomet. Chem. 1973, 54, 87.
34. 4] in ca. 78% yield.
35. Sutton, L. E. Interatomic Distances and Configuration in Molecules and Ions; Special Publications No. 18; The Chemical Society: London, 1965.
36. Levine, I. R. J. Chem. Phys. 1963, 38, 2326.
37. Waggoner, K. M.; Power, P. P. J. Am. Chem. Soc. 1991, 113, 3385.
38. Coles, M. P.; Swenson, D. C.; Jordan, R. F. Organometallics 1997, 16, 5184.
39. Kanters, J. A.; Van Mier, G. P. M.; Nijs, R. L. L. M.; Van Der Steen, F.; Van Koten, G. Acta Crystallogr. C 1988, 44, 1391.
40. (a) Burgess, K.; Holden, D. H.; Johnson, B. F. G.; Lewis, J. J. Chem Soc., Dalton Trans. 1983, 1199.
41. (b) Deeming, A. J.; Peters, R. J. Organomet. Chem. 1980, 202, C39.
42. Hausen, H. D.; Gerstner, F.; Schwarz, W. J. Organomet. Chem. 1978, 145, 277.
43. 3].
44. 14N, 99.36% abundance, I= 1) on the spectra of spin 1/2 nuclei is described in the following: Harris, R. K. Nuclear Magnetic Spectroscopy; Longman Scientific & Technical: Essex, UK, 1986; pp 139-140.
45. 3. See: Lehn, J. M.; Kintzinger, J. P. In Nitrogen NMR; Witanowski, M., Webb, G. A., Eds.; Plenum: London, 1973; Chapter 3, pp 124-127.
46. iPr-CH signals at -85°C does not complicate the simulation of the spectra.
47. coal. = 217(2) K, ΔG‡ = 9.5(7) kcal/mol.
48. The activation parameters were obtained from the Eyring equation: In(k/T) = (-ΔH‡/R)/T + 23.76 + ΔS‡/R, using a least-squares fit of In(k/ T) vs I/T (m = -ΔH‡/R, b = 23.76 + ΔS‡/R).
49. 26
50. Skoog, D. A.; Leary, J. J. Principles of Instrumental Analysis, 4th ed.; Saunders College: New York, 1992; pp A13-14.
51. Henrickson, C. H.; Duffy, D.; Eyman, D. P. Inorg. Chem. 1968, 7, 1047.
52. Barker, J.; Cameron, N.; Kilner, M.; Mahoud, M. M.; Wallwork, S. C. J. Chem. Soc., Dalton Trans. 1986, 1359.
53. -1, ΔG‡ = 11.7(3) kcal/mol. Similar estimates for the exchange barrier for process (ii) were obtained from the analysis of the line broadening of the AlMe resonance between 223 and 239 K (ΔG‡ ≈ 11.7 kcal/mol).
54. Ham, N. S.; Mole, T. In Progress in NMR Spectroscopy; Emsley, J. W., Feeney, J., Sutcliffe, V., Eds.; Pergamon: New York, NY, 1969; Vol. 4, p 128.
55. + was estimated from the line broadening of the bridging Al-Me resonance at 190 K (ΔG‡ ≈ 8.5(4) kcal/mol).
56. 3] except for the anion resonances.
57. + (ΔG‡ = 11.7(3) kcal/mol).
58. 1H NMR).
59. 4] confirmed this assignment.
60. 4] and 6a is slow on the NMR time scale under these conditions.
61. 4] in ca. 64% yield.
62. Bregadze, V. I.; Furmanova, N. G.; Golubinskaya, L. M.; Kompan, O. Y.; Struchkov, Y. T. J. Organomet. Chem. 1980, 192, 1.
63. Atwood, D. A.; Jones, R. A.; Cowley, A. H., Bott, S. G.; Atwood, J. L. J. Organomet. Chem. 1993, 453, 24.
64. Dagorne, S.; Young, V. G., Jr.; Jordan, R. F. Manuscript in preparation.
65. Atwood, D. A.; Jones, R. A.; Cowley, A. H.; Bott, S. G.; Atwood, J. L. J. Organomet. Chem. 1992, 425, C1.
66. + and 6b is slow on the NMR time scale.
67. iPr-CH resonance that are significantly broader than the other resonances of the same type, which is consistent with the presence of one four-coordinate nitrogen and three three-coordinate nitrogens.
68. 4] yields undentified species.
69. 2. See: Wrackmeyer, B.; Nöth, H. Chem. Ber. 1976, 109, 1075.
70. 2. See: Wrackmeyer, B.; Nöth, H. Chem. Ber. 1976, 109, 1075.
71. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
72. Malone, J. F.; McDonald, W. S. J. Chem. Soc., Dalton Trans. 1972, 2646.
73. 5Cl at 80°C confirmed this assignment.
74. 1H NMR) and unidentified boron species.
75. (a) For synthesis of mono-amidinate group 13 dialkyl complexes by salt metathesis routes, see: Kottmair-Maieron, D.; Leehter, R.; Weidlein, J. Z. Anorg. Allg. Chem. 1991, 593, 111.
76. (b) For the synthesis of 12b, see ref 41.
77. The Ga analogues exhibit very similar structural trends.
78. iPr substituent; see ref 17.
79. Zhou, Y.; Richeson, D. S. Inorg. Chem. 1996, 35, 1423.
80. (a) Chien, J. C. W.; Tsai, W. M.; Rausch, M. D. J. Am. Chem. Soc. 1991, 113, 8570.
81. (b) See also ref 4b.
82. 5).
83. 5Cl, 80 °C): δ 61 (br).
84. - resonance was obscured by the solvent resonances.
85. - resonance was obscured by the solvent resonances.
86. 2 resonances are significantly overlapped and therefore are not listed here.
87. Pople, J. A.; Schneider, W. G.; Bernstein, H. J. High-Resolution Nuclear Magnetic Resonance; McGraw-Hill: New York, NY, 1959.
88. (a) Binsch, G. In Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., and Cotton, F. A., Eds.; Academic Press: London, 1975; p 45.
89. (b) Steigel, A. In NMR, Basic Principles and Progress; Diehl, P., Fluck, E., Kosfeld, R., Eds.; Springer-Verlag: Berlin, 1978; Vol. 15, p 1.
90. (a) Binsch, G. J. Am. Chem. Soc. 1969, 91, 1304.
91. (b) Stephenson, D. S.; Binsch, G. J. Magn. Reson. 1978, 30, 625.