Neutral and cationic group 4 metal compounds containing octamethyldibenzotetraazaannulene (Me8taa2-) ligands. Synthesis and reactivity of (Me8taa)MX2 and (Me8taa)MX+ complexes (M = Zr, Hf; X = Cl, hydrocarbyl, NR2, OR)

Organometallics

Volumn 17, Issue 3, 1998, Pages 382-397

  Martin, Alfredo ^a   Uhrhammer, Roger ^a   Gardner, Thomas G ^a   Jordan, Richard F ^a   Rogers, Robin D ^b  

^a University of Iowa ^*  (United States)

^b UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000419140     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970814x     Document Type: Article

References (164)

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20. For reviews concerning the chemistry of cationic group 4 metallocene complexes, see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
21. For reviews concerning the chemistry of cationic group 4 metallocene complexes, see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
22. For reviews concerning the chemistry of cationic group 4 metallocene complexes, see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
23. For reviews concerning the chemistry of cationic group 4 metallocene complexes, see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
24. For reviews concerning the chemistry of cationic group 4 metallocene complexes, see: (a) Guram, A. S.; Jordan, R. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: Oxford, 1995; Vol. 4, p 589. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Horton, A. D. Trends Polym. Sci. 1994, 2, 158. (d) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (e) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325. (f) Jordan, R. F.; Bradley, P. K.; Lapointe, R. E.; Taylor, D. F. New J. Chem. 1990, 14, 505.
25. For a preliminary communication, see: Uhrhammer, R.; Black, D. G.; Gardner, T. G.; Olsen, J. D.; Jordan, R. F. J. Am. Chem. Soc. 1993, 115, 8493.
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33. (c) Goedken, V. L.; Weiss, M. C. Inorg. Synth. 1980, 20, 115.
34. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
35. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
36. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
37. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
38. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
39. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
40. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
41. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
42. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
43. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
44. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
45. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
46. For related work concerning group 4 metal porphyrin complexes, see: (a) Brand, H.; Capriotti, J. A.; Arnold, J. Organometallics 1994, 13, 4469. (b) Brand, H.; Arnold, J. Organometallics 1993, 12, 3655. (c) Arnold, J.; Johnson, S. E.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 3996. (d) Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266. (e) Brand, H.; Arnold, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 95. (f) Shibata, K.; Aida, J.; Inoue, S. Tetrahedron Lett. 1992, 33, 1077. (g) Shibata, K.; Aida, T.; Inoue, S. Chem. Lett. 1992, 1173. (h) Woo, L. K.; Hays, J. A.; Jacobson, R. A; Day, C. L. Organometallics 1991, 10, 2102. (i) Latour, J.; Boreham, C. J.; Marchon, J. J. Organomet. Chem. 1990, 190, C61. (j) Ryu, S.; Whang, D.; Kim, J.; Yeo, W.; Kim, K. J. Chem. Soc., Dalton Trans. 1993, 205. (k) Kim, H.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360. (l) Kim, H.-J.; Whang, D.; Do, Y.; Kim, K. Chem. Lett. 1993, 807. (m) Kim, K.; Lee, W. S.; Kim, H.-J.; Cho, S.-H.; Girolami, G. S.; Gorlin, P. A.; Suslick, K. S. Inorg. Chem. 1991, 30, 2652.
47. 2 complexes, see: (a) Black, D. G.; Swenson, D. C.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3539. (b) Black, D. G.; Jordan, R. F.; Rogers, R. D. Inorg. Chem. 1997, 36, 103.
48. 2 complexes, see: (a) Black, D. G.; Swenson, D. C.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3539. (b) Black, D. G.; Jordan, R. F.; Rogers, R. D. Inorg. Chem. 1997, 36, 103.
49. 2.
50. For leading references, see ref 9a and (a) Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
51. Finch, W. C.; Anslyn, E. V.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 2406.
52. CH values, see: Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424 and references therein.
53. (a) Hunter, W. E.; Hrncir, D. C.; Bynum, R. V.; Penttila, R. A.; Atwood, J. L. Organometallics 1983, 2, 750.
54. (b) Green, M. L. H.; Hughes, A. K.; Popham, N. A.; Stephens, A. H. D.; Wong, L.-L. J. Chem. Soc., Dalton Trans. 1992, 3077.
55. For agostic interactions, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1. (b) Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. (c) Ginzburg, A. S. Russ. Chem. Rev. 1988, 57, 1175. (d) Cotton, F. A.; Luck, R. L. Inorg. Chem. 1989, 28, 3210. (e) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K.; Schultz, A. J.; Williams, J. M.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1986, 1629.
56. For agostic interactions, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1. (b) Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. (c) Ginzburg, A. S. Russ. Chem. Rev. 1988, 57, 1175. (d) Cotton, F. A.; Luck, R. L. Inorg. Chem. 1989, 28, 3210. (e) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K.; Schultz, A. J.; Williams, J. M.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1986, 1629.
57. For agostic interactions, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1. (b) Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. (c) Ginzburg, A. S. Russ. Chem. Rev. 1988, 57, 1175. (d) Cotton, F. A.; Luck, R. L. Inorg. Chem. 1989, 28, 3210. (e) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K.; Schultz, A. J.; Williams, J. M.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1986, 1629.
58. For agostic interactions, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1. (b) Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. (c) Ginzburg, A. S. Russ. Chem. Rev. 1988, 57, 1175. (d) Cotton, F. A.; Luck, R. L. Inorg. Chem. 1989, 28, 3210. (e) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K.; Schultz, A. J.; Williams, J. M.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1986, 1629.
59. For agostic interactions, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1. (b) Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. (c) Ginzburg, A. S. Russ. Chem. Rev. 1988, 57, 1175. (d) Cotton, F. A.; Luck, R. L. Inorg. Chem. 1989, 28, 3210. (e) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K.; Schultz, A. J.; Williams, J. M.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1986, 1629.
60. n-benzyl bonding see ref 9c and references therein.
61. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
62. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
63. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
64. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
65. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
66. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
67. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
68. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
69. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
70. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
71. For reviews and selected examples, see: (a) Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis Horwood: Chichester, West Sussex, 1980. (b) Bradley, D. C. Adv. Inorg. Chem. Radiochem. 1972, 15, 259. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (d) Bowen, D. E.; Jordan, R. F.; Rogers, R. D. Organometallics 1995, 14, 3630. (e) Duan, Z.; Verkade, J. G. Inorg. Chem. 1995, 34, 4311. (f) Galakhov, M.; Martin, A.; Mena, M.; Yelamos, C. J. Organomet. Chem. 1995, 496, 217. (g) Hughes, A. K.; Meetsama, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (h) Bürger, H.; Dämmgen, U. J. Organomet. Chem. 1975, 101, 295. (i) Dämmgen, U.; Bürger, H.; J. Organomet. Chem. 1975, 101, 307. (j) Jenkins, A. D.; Lappert, M. F.; Srivastava, A. C. J. Organomet. Chem. 1970, 23, 165. (k) Chandra, G.; Lappert, M. F. J. Chem. Soc. A 1968, 1940.
72. (a) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1996, 118, 8024.
73. (b) Christopher, J. N.; Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4038.
74. (c) Kim, I.; Jordan, R. F. Macromolecules 1996, 29, 489.
75. See ref 21 and (a) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4045. (b) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4030.
76. See ref 21 and (a) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4045. (b) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4030.
77. (a) McLaughlin, G. M.; Sim, G. A.; Smith, J. D. J. Chem. Soc., Dalton Trans. 1972, 2197.
78. (b) Al-Wassil, A. I.; Hitchcock, P. B.; Sarisaban, S.; Smith, J. D.; Wilson, C. L. J. Chem. Soc., Dalton Trans. 1985, 1929.
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82. (f) Amero, B. A.; Schram, E. P. Inorg. Chem. 1976, 15, 2842.
83. -, see: Oliver, J. P.; Wilkie, C. A. J. Am. Chem. Soc. 1967, 89, 104.
84. C-H values quoted in the text, which are in agreement with those reported in Yamamoto, O. Chem. Lett. 1975, 511.
85. (a) Lehmkuhl, H.; Eisenbach, W. Justus Liebigs Ann. Chem. 1967, 705, 42.
86. (b) Lehmkuhl, H.; Kobs, H.-D. Justus Liebigs Ann. Chem. 1968, 719, 11.
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91. (g) Richey, H. G., Jr.; BergStresser, G. L. Organometallics 1988, 7, 1459.
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96. (l) Emig, N.; Réau, R.; Krautscheid, H.; Fenske, D.; Bertrand, G. J. Am. Chem. Soc. 1996, 118, 5822.
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99. (a) Turner, H. W.; Hlatky, G. G. Eur. Pat. Appl. 0 277 004, 1988.
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103. (e) Bochmann, M.; Lancaster, S. J. Organometallics 1993, 12, 633.
104. (f) Lin, Z.; Le Marechal, J.; Sabat, M.; Marks, T. J. J. Am. Chem. Soc. 1987, 109, 4127.
105. (g) Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1991, 10, 840.
106. Jordan, R. F.; LaPointe, R. E.; Bajgur, C. S.; Echols, S. F.; Willett, R. D. J. Am. Chem. Soc. 1987, 109, 4111.
107. 2 were observed at -80°C, which indicates that solvent is either not coordinated, or that exchange of coordinated and free solvent is rapid at this temperature. See: (a) Fernández, J.; Gladysz, J. A. Organometallics 1989, 8, 207. (b) Huang, D.; Huffman, J. C.; Bollinger, J. C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (c) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89 and references therein.
108. 2 were observed at -80°C, which indicates that solvent is either not coordinated, or that exchange of coordinated and free solvent is rapid at this temperature. See: (a) Fernández, J.; Gladysz, J. A. Organometallics 1989, 8, 207. (b) Huang, D.; Huffman, J. C.; Bollinger, J. C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (c) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89 and references therein.
109. 2 were observed at -80°C, which indicates that solvent is either not coordinated, or that exchange of coordinated and free solvent is rapid at this temperature. See: (a) Fernández, J.; Gladysz, J. A. Organometallics 1989, 8, 207. (b) Huang, D.; Huffman, J. C.; Bollinger, J. C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (c) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89 and references therein.
110. 1 distance is significantly shorter than the Zr-C2 distance. See: (a) Wu, Z.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867. (b) Strömberg, S.; Christopher, J. C.; Lee, C. W.; Swenson, D. C.; Jordan, R. F. Manuscript in preparation.
111. 1 distance is significantly shorter than the Zr-C2 distance. See: (a) Wu, Z.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867. (b) Strömberg, S.; Christopher, J. C.; Lee, C. W.; Swenson, D. C.; Jordan, R. F. Manuscript in preparation.
112. Kuchta, M.; Parkin, G. J. Chem. Soc., Chem. Commun. 1994, 1351.
113. Weiss, M. C.; Goedken, V. L. Inorg. Chem. 1979, 18, 819.
114. Mandon, D.; Giraudon, J.; Toupet, L.; Sala-Pala, J.; Guerchais, E. J. Am. Chem. Soc. 1987, 109, 3490.
115. Edema, J. J. H.; Gambarotta, S.; van der Sluis, P.; Smeets, W. J. J.; Spek, A. L. Inorg. Chem. 1989, 28, 3784.
116. Cotton, F. A.; Czuchajowska, J.; Feng, X. Inorg. Chem. 1990, 29, 4329.
117. Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8.
118. (a) Horton, A. D.; Orpen, A. G. Organometallics 1992, 11, 8.
119. (b) Guram, A. S.; Jordan, R. F. Organometallics 1991, 10, 3470.
120. Eisch, J. J.; Piotrowski, A. M.; Brownstein, S. K.; Gabe, E. J.; Lee, F. L. J. Am. Chem. Soc. 1985, 107, 7219.
121. + was ascribed to stabilization by the Zr- - -Ph interaction, see: Wang, Y.; Jordan, R. F.; Echols, S. F.; Borkowsky, S. L.; Bradley, P. K. Organometallics 1991, 10, 1406.
122. (a) Eisch, J. J.; Caldwell, K. R.; Werner, S.; Krüger, C. Organometallics 1991, 10, 3417.
123. (b) Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1988, 110, 108.
124. (c) Guram, A. S.; Jordan, R. F. Organometallics 1990, 9, 2190.
125. Kumar, P. N. V. P.; Jemmis, E. D. J. Am. Chem. Soc. 1988, 110, 125 and references therein.
126. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
127. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
128. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
129. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
130. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
131. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
132. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
133. For representative examples, see: (a) Forsyth, C. M.; Nolan, S. P.; Stern, C. L.; Marks, T. J. Organometallics 1993, 12, 3618. (b) Shen, Q.; Zheng, D.; Lin, L.; Lin, Y. J. Organomet. Chem. 1990, 391, 307. (c) Boncella, J. M.; Tilley, T. D.; Andersen, R. A. J. Chem. Soc., Chem. Commun. 1984, 710. (d) Evans, W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. Organometallics 1983, 2, 709. (e) Atwood, J. L.; Hunter, W. E.; Wayda, A. L.; Evans, W. J. Inorg. Chem. 1981, 20, 4115. (f) Lee, L.; Berg, D. J.; Bushnell, G. W. Organometallics 1995, 14, 5021. (g) Almenningen, A.; Fernholt, L.; Haaland, A. J. Organomet. Chem. 1978, 155, 245. (h) Morosin, B.; Howatson, J. J. Organomet. Chem. 1971, 29, 7.
134. 2Zr examples, see: (a) Röttger, D.; Erker, G.; Fröhlich, R.; Grehl, M.; Silverio, S. J.; Hyla-Kryspin, I.; Gleiter, R. J. Am. Chem. Soc. 1995, 117, 10503. (b) Horton, A. D.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 876.
135. 2Zr examples, see: (a) Röttger, D.; Erker, G.; Fröhlich, R.; Grehl, M.; Silverio, S. J.; Hyla-Kryspin, I.; Gleiter, R. J. Am. Chem. Soc. 1995, 117, 10503. (b) Horton, A. D.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 876.
136. For representative examples, see: (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Angermund, K.; Krüger, C. Organometallics 1989, 8, 911. (b) Rosenthal, U.; Pulst, S.; Arndt, P.; Ohff, A.; Tillac, A.; Baumann, W.; Kempe, R.; Burkalov, V. V. Organometallics 1995, 14, 2961. (c) Erker, G.; Frömberg, W.; Mynott, R.; Gabor, B.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 463. (d) Cowie, M.; Loeb, S. J. Organometallics 1985, 4, 852.
137. For representative examples, see: (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Angermund, K.; Krüger, C. Organometallics 1989, 8, 911. (b) Rosenthal, U.; Pulst, S.; Arndt, P.; Ohff, A.; Tillac, A.; Baumann, W.; Kempe, R.; Burkalov, V. V. Organometallics 1995, 14, 2961. (c) Erker, G.; Frömberg, W.; Mynott, R.; Gabor, B.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 463. (d) Cowie, M.; Loeb, S. J. Organometallics 1985, 4, 852.
138. For representative examples, see: (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Angermund, K.; Krüger, C. Organometallics 1989, 8, 911. (b) Rosenthal, U.; Pulst, S.; Arndt, P.; Ohff, A.; Tillac, A.; Baumann, W.; Kempe, R.; Burkalov, V. V. Organometallics 1995, 14, 2961. (c) Erker, G.; Frömberg, W.; Mynott, R.; Gabor, B.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 463. (d) Cowie, M.; Loeb, S. J. Organometallics 1985, 4, 852.
139. For representative examples, see: (a) Erker, G.; Frömberg, W.; Benn, R.; Mynott, R.; Angermund, K.; Krüger, C. Organometallics 1989, 8, 911. (b) Rosenthal, U.; Pulst, S.; Arndt, P.; Ohff, A.; Tillac, A.; Baumann, W.; Kempe, R.; Burkalov, V. V. Organometallics 1995, 14, 2961. (c) Erker, G.; Frömberg, W.; Mynott, R.; Gabor, B.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 463. (d) Cowie, M.; Loeb, S. J. Organometallics 1985, 4, 852.
140. Horton, A. D. J. Chem. Soc., Chem. Commun. 1992, 185.
141. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.;
142. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruchter, G. J. Am. Chem. Soc. 1997, 119, 698. (g) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
143. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruchter, G. J. Am. Chem. Soc. 1997, 119, 698. (g) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
144. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruchter, G. J. Am. Chem. Soc. 1997, 119, 698. (g) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
145. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruchter, G. J. Am. Chem. Soc. 1997, 119, 698. (g) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
146. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruchter, G. J. Am. Chem. Soc. 1997, 119, 698. (g) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
147. For leading references, see: (a) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053. (b) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (c) Straub, T.; Haskel, A.; Eisen, M. S. J. Am. Chem. Soc. 1995, 117, 6364. (d) St. Clair, M.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1991, 10, 525. (e) Heeres, H. J.; Nijhoff, J.; Teuben, J. H.; Rogers, R. D. Organometallics 1993, 12, 2609. For alkyne oligomerization by late metal complexes, see: (f) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruchter, G. J. Am. Chem. Soc. 1997, 119, 698. (g) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
148. For Ti catalyst, see: (a) Akita, M.; Yasuda, H.; Nakamura, A. Bull. Chem. Soc. Jpn. 1984, 57, 480. (b) Varga, V.; Petrusová, L.; Cejka, J.; Hanus, V.; Mach, K. J. Organomet. Chem. 1996, 509, 235.
149. For Ti catalyst, see: (a) Akita, M.; Yasuda, H.; Nakamura, A. Bull. Chem. Soc. Jpn. 1984, 57, 480. (b) Varga, V.; Petrusová, L.; Cejka, J.; Hanus, V.; Mach, K. J. Organomet. Chem. 1996, 509, 235.
150. Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508.
151. (a) Scollard, J. D.; McConville, D. H. J. Am. Chem. Soc. 1996, 118, 10008.
152. (b) Scollard, J. D.; McConville, D. H.; Payne, N. C.; Vittal, J. J. Macromolecules 1996, 29, 5241.
153. (c) Baumann, R.; Davis, W. M.; Schrock, R. R. J. Am. Chem. Soc. 1997, 119, 3830.
154. (d) Horton, A. D.; de With, J.; van der Linden, A. J.; van de Weg, H. Organometallics 1996, 15, 2672.
155. (e) van der Linden, A. J.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem. Soc. 1995, 117, 3008.
156. Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291.
157. Collier, M. R.; Lappert, M. F. J. Chem Soc., Dalton Trans. 1973, 445.
158. Zucchini, U.; Aldizzati, E.; Giannini, U. J. Organomet. Chem. 1971, 26, 357.
159. Manzer, L. E. Inorg. Synth. 1982, 21, 135.
160. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245.
161. CF = 244), 122.6 (br m, BC).
162. BC = 49, ipso), 136.2, 126.0, 122.2.
163. 2Ph).
164. 2) δ 2.32 (m, 6 H), 1.30 (m, 12 H), 0.91 (t, J = 7, 9 H).