Formation of hypercoordinated carbon inside a (μ-hydrocarbyl)bis(group 4 metallocene) framework by a simple protonation route

Journal of the American Chemical Society

Volumn 120, Issue 21, 1998, Pages 5264-5273

  Schottek, Jörg ^a   Röttger, Dirk ^a   Erker, Gerhard ^a   Fröhlich, Roland ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; CARBON; LIGAND; METAL COMPLEX; UNCLASSIFIED DRUG; ZIRCONOCENE;

ARTICLE; CRYSTAL STRUCTURE; GEOMETRY; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS; THERMODYNAMICS;

EID: 2642647091     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980223d     Document Type: Article

References (107)

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7. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930. Scherbaum, F.; Grohmann, A.; Huber, B.; Krüger, C.; Schmidbaur, H. Angew. Chem. 1988, 100, 1602; Angew. Chem., Int. Ed. Engl. 1988, 27, 1544. Scherbaum, F.; Grohmann, A.; Müller, G.; Schmidbaur, H. Angew. Chem. 1989, 101, 464; Angew. Chem., Int. Ed. Engl. 1989, 28, 463. Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. Organometallics 1990, 9, 2843. Schmidbaur, H.; Brachthäuser, B.; Steigelmann, O. Angew. Chem. 1991, 103, 1552; Angew. Chem., Int. Ed. Engl. 1991, 30, 1488. Glukhovtsev, M. N.; Simkin, B. Ya., Minkin, V. I. J. Org. Chem. USSR 1991, 27, 1. Dufour, N.; Schier, A,; Schmidbaur, H. Organometallics 1993, 12, 2408. Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266. Schmidbaur, H.; Gabbai, F. P.; Schier, A.; Riede, J. Organometallics 1995, 14, 4969. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737 and references cited in these articles. Many examples of organometallic compounds containing hypercoordinated C atoms are found in the following: Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
8. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930. Scherbaum, F.; Grohmann, A.; Huber, B.; Krüger, C.; Schmidbaur, H. Angew. Chem. 1988, 100, 1602; Angew. Chem., Int. Ed. Engl. 1988, 27, 1544. Scherbaum, F.; Grohmann, A.; Müller, G.; Schmidbaur, H. Angew. Chem. 1989, 101, 464; Angew. Chem., Int. Ed. Engl. 1989, 28, 463. Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. Organometallics 1990, 9, 2843. Schmidbaur, H.; Brachthäuser, B.; Steigelmann, O. Angew. Chem. 1991, 103, 1552; Angew. Chem., Int. Ed. Engl. 1991, 30, 1488. Glukhovtsev, M. N.; Simkin, B. Ya., Minkin, V. I. J. Org. Chem. USSR 1991, 27, 1. Dufour, N.; Schier, A,; Schmidbaur, H. Organometallics 1993, 12, 2408. Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266. Schmidbaur, H.; Gabbai, F. P.; Schier, A.; Riede, J. Organometallics 1995, 14, 4969. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737 and references cited in these articles. Many examples of organometallic compounds containing hypercoordinated C atoms are found in the following: Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
9. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930. Scherbaum, F.; Grohmann, A.; Huber, B.; Krüger, C.; Schmidbaur, H. Angew. Chem. 1988, 100, 1602; Angew. Chem., Int. Ed. Engl. 1988, 27, 1544. Scherbaum, F.; Grohmann, A.; Müller, G.; Schmidbaur, H. Angew. Chem. 1989, 101, 464; Angew. Chem., Int. Ed. Engl. 1989, 28, 463. Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. Organometallics 1990, 9, 2843. Schmidbaur, H.; Brachthäuser, B.; Steigelmann, O. Angew. Chem. 1991, 103, 1552; Angew. Chem., Int. Ed. Engl. 1991, 30, 1488. Glukhovtsev, M. N.; Simkin, B. Ya., Minkin, V. I. J. Org. Chem. USSR 1991, 27, 1. Dufour, N.; Schier, A,; Schmidbaur, H. Organometallics 1993, 12, 2408. Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266. Schmidbaur, H.; Gabbai, F. P.; Schier, A.; Riede, J. Organometallics 1995, 14, 4969. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737 and references cited in these articles. Many examples of organometallic compounds containing hypercoordinated C atoms are found in the following: Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
10. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930. Scherbaum, F.; Grohmann, A.; Huber, B.; Krüger, C.; Schmidbaur, H. Angew. Chem. 1988, 100, 1602; Angew. Chem., Int. Ed. Engl. 1988, 27, 1544. Scherbaum, F.; Grohmann, A.; Müller, G.; Schmidbaur, H. Angew. Chem. 1989, 101, 464; Angew. Chem., Int. Ed. Engl. 1989, 28, 463. Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. Organometallics 1990, 9, 2843. Schmidbaur, H.; Brachthäuser, B.; Steigelmann, O. Angew. Chem. 1991, 103, 1552; Angew. Chem., Int. Ed. Engl. 1991, 30, 1488. Glukhovtsev, M. N.; Simkin, B. Ya., Minkin, V. I. J. Org. Chem. USSR 1991, 27, 1. Dufour, N.; Schier, A,; Schmidbaur, H. Organometallics 1993, 12, 2408. Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266. Schmidbaur, H.; Gabbai, F. P.; Schier, A.; Riede, J. Organometallics 1995, 14, 4969. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737 and references cited in these articles. Many examples of organometallic compounds containing hypercoordinated C atoms are found in the following: Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
11. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930. Scherbaum, F.; Grohmann, A.; Huber, B.; Krüger, C.; Schmidbaur, H. Angew. Chem. 1988, 100, 1602; Angew. Chem., Int. Ed. Engl. 1988, 27, 1544. Scherbaum, F.; Grohmann, A.; Müller, G.; Schmidbaur, H. Angew. Chem. 1989, 101, 464; Angew. Chem., Int. Ed. Engl. 1989, 28, 463. Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. Organometallics 1990, 9, 2843. Schmidbaur, H.; Brachthäuser, B.; Steigelmann, O. Angew. Chem. 1991, 103, 1552; Angew. Chem., Int. Ed. Engl. 1991, 30, 1488. Glukhovtsev, M. N.; Simkin, B. Ya., Minkin, V. I. J. Org. Chem. USSR 1991, 27, 1. Dufour, N.; Schier, A,; Schmidbaur, H. Organometallics 1993, 12, 2408. Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266. Schmidbaur, H.; Gabbai, F. P.; Schier, A.; Riede, J. Organometallics 1995, 14, 4969. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737 and references cited in these articles. Many examples of organometallic compounds containing hypercoordinated C atoms are found in the following: Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
12. Schleyer, P. v. R.; Würthwein, E.-U.; Kaufmann, E.; Clark T.; Pople, J. A. J. Am. Chem. Soc. 1983, 105, 5930. Scherbaum, F.; Grohmann, A.; Huber, B.; Krüger, C.; Schmidbaur, H. Angew. Chem. 1988, 100, 1602; Angew. Chem., Int. Ed. Engl. 1988, 27, 1544. Scherbaum, F.; Grohmann, A.; Müller, G.; Schmidbaur, H. Angew. Chem. 1989, 101, 464; Angew. Chem., Int. Ed. Engl. 1989, 28, 463. Waymouth, R. W.; Potter, K. S.; Schaefer, W. P.; Grubbs, R. H. Organometallics 1990, 9, 2843. Schmidbaur, H.; Brachthäuser, B.; Steigelmann, O. Angew. Chem. 1991, 103, 1552; Angew. Chem., Int. Ed. Engl. 1991, 30, 1488. Glukhovtsev, M. N.; Simkin, B. Ya., Minkin, V. I. J. Org. Chem. USSR 1991, 27, 1. Dufour, N.; Schier, A,; Schmidbaur, H. Organometallics 1993, 12, 2408. Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. Organometallics 1994, 13, 4266. Schmidbaur, H.; Gabbai, F. P.; Schier, A.; Riede, J. Organometallics 1995, 14, 4969. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737 and references cited in these articles. Many examples of organometallic compounds containing hypercoordinated C atoms are found in the following: Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
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17. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
18. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
19. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
20. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
21. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
22. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
23. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
24. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
25. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
26. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
27. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
28. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
29. Sinn, H.; Kolk, E. J. Organomet. Chem. 1966, 6, 373. Kaminsky, W.; Sinn, H. Liebigs Ann. Chem. 1975, 424. Kaminsky, W.; Kopt, J.; Sinn, H.; Vollmer, H.-J. Angew. Chem. 1976, 88, 688. Cotton, F. A.; Kibala, P. A. Polyhedron 1987, 6, 645. McDade, C.; Gibson, V. C.; Santarsiero, B. D.; Bercaw, J. Organometallics 1988, 7, 1. Cotton, F. A.; Kibala, P. A. Inorg. Chem. 1990, 29, 3192. Negishi, E.; Nakajima, K.; Takahashi, T.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 3413. Bochmann, M.; Robinson, O. B.; Lancaster, S. J.; Hursthouse, M. B.; Coles, S. J. Organometallics 1995, 14, 2456. Sun, Y.; Piers, W. E.; Retting, S. J. Organometallics 1996, 15, 4110. Karl, J.; Erker, G.; Fröhlich, R.; Zippel, F.; Bickelhaupt, F.; Schreuder Goedheijt, M.; Akkerman, O. S.; Binger, P.; Stannek, J. Angew. Chem. 1997, 109, 2914: Angew. Chem., Int. Ed. Engl. 1997, 36, 2771. Schottek, J.; Erker, G.; Fröhlich, R.; Angew. Chem. 1997, 109, 2585; Angew. Chem., Int. Ed. Engl. 1997, 36, 2475.
30. We had previously used a selective protonation reaction of dinuclear (μ-acetylide)bis(zirconocene) complexes to obtain examples of stable planartetracoordinate carbon compounds: Schottek, J.; Erker, G.; Fröhlich, R. Eur. J. Inorg. Chem., in press.
31. (a) Erker, G.; Kropp, K.; Atwood, J. L.; Hunter, W. E. Organometallics 1983, 2, 1555.
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35. Cayne, F. E. Anal. Chem. 1956, 28, 1794. Bochmann, M.; Jaggar, A. J.; Nicholls, J. C. Angew. Chem. 1990, 102, 830; Angew. Chem., Int. Ed. Engl. 1990, 29, 780. Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255 and references therein. See also: Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325
36. Cayne, F. E. Anal. Chem. 1956, 28, 1794. Bochmann, M.; Jaggar, A. J.; Nicholls, J. C. Angew. Chem. 1990, 102, 830; Angew. Chem., Int. Ed. Engl. 1990, 29, 780. Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255 and references therein. See also: Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325
37. Cayne, F. E. Anal. Chem. 1956, 28, 1794. Bochmann, M.; Jaggar, A. J.; Nicholls, J. C. Angew. Chem. 1990, 102, 830; Angew. Chem., Int. Ed. Engl. 1990, 29, 780. Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255 and references therein. See also: Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325
38. Cayne, F. E. Anal. Chem. 1956, 28, 1794. Bochmann, M.; Jaggar, A. J.; Nicholls, J. C. Angew. Chem. 1990, 102, 830; Angew. Chem., Int. Ed. Engl. 1990, 29, 780. Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255 and references therein. See also: Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325
39. (a) Wailes, P. C.; Weigold, H.; Bell, A. P. J. Organomet. Chem. 1971, 27, 373. Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679. Labinger, J. A.; Hart, D. W.; Seibert, W. E.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 3851. Schwartz, J. Labinger, J. A. Angew. Chem. 1976, 88, 402. Yoshifuji, M.; Loots, M. J.; Schwartz, J. Tetrahedron Lett. 1977, 1303. Okukado, N.; Van Horn, D. E.; Klima, W. L.; Negishi, E. I. Tetrahedron Lett. 1978, 1027. Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521. Schwartz, J. Pure Appl. Chem. 1980, 52, 733. Matsushita, H.; Negishi, E. I. J. Am. Chem. Soc. 1981, 103, 2882. Temple, J. S.; Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 1310. Negishi, E. I.; Takahashi, T. Aldrichim. Acta 1985, 18, 31. Erker, G.; Schlund, R.; Krüger, C. Organometallics 1989, 8, 2349.
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102. (b) Ivin, K. J.; Rooney, J. J.; Stewart, C. D.; Green, M. L. H.; Mahtab, R. J. Chem. Soc., Chem. Commun. 1978, 604. Green, M. L. H. Pure Appl. Chem. 1978, 50, 27. Laverty, D. T.; Rooney, J. J. J. Chem. Soc., Faraday Trans. 1 1983, 79, 869. Brookhart, M.; Green, M. L. H.; Pardy, R. B. A. J. Chem. Soc., Chem. Commun. 1983, 691. Clawson, L.; Soto, J.; Buchwald, S. L.; Steigerwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985, 107, 3377. Piers, W. E.; Bercaw, J. E. J. Am. Chem Soc. 1990, 112, 9406. Krandelat, H.; Brintzinger, H.-H. Angew. Chem. Soc. 1990, 102, 1459; Angew. Chem., Int. Ed. Engl. 1990, 29, 1412. Janiak, B. J. Organomet. Chem. 1993, 452, 63. Barta, N. S.; Kirk, B. A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 8912. Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651, 1996, 118, 9024. Prosenc, M.-H.; Brintzinger, H.-H. Organometallics 1997, 16, 3889. Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. Alelyunas, Y. W.; Gou, Z.; LaPointe, R. E. Jordan, R. F. Organometallics 1993, 12, 544. Alelyunas, Y. W.; Baenziger, N. C.; Bradley, P. K.; Jordan, R. F. Organometallics 1994, 13, 148. Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424.
103. (b) Ivin, K. J.; Rooney, J. J.; Stewart, C. D.; Green, M. L. H.; Mahtab, R. J. Chem. Soc., Chem. Commun. 1978, 604. Green, M. L. H. Pure Appl. Chem. 1978, 50, 27. Laverty, D. T.; Rooney, J. J. J. Chem. Soc., Faraday Trans. 1 1983, 79, 869. Brookhart, M.; Green, M. L. H.; Pardy, R. B. A. J. Chem. Soc., Chem. Commun. 1983, 691. Clawson, L.; Soto, J.; Buchwald, S. L.; Steigerwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985, 107, 3377. Piers, W. E.; Bercaw, J. E. J. Am. Chem Soc. 1990, 112, 9406. Krandelat, H.; Brintzinger, H.-H. Angew. Chem. Soc. 1990, 102, 1459; Angew. Chem., Int. Ed. Engl. 1990, 29, 1412. Janiak, B. J. Organomet. Chem. 1993, 452, 63. Barta, N. S.; Kirk, B. A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 8912. Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651, 1996, 118, 9024. Prosenc, M.-H.; Brintzinger, H.-H. Organometallics 1997, 16, 3889. Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. Alelyunas, Y. W.; Gou, Z.; LaPointe, R. E. Jordan, R. F. Organometallics 1993, 12, 544. Alelyunas, Y. W.; Baenziger, N. C.; Bradley, P. K.; Jordan, R. F. Organometallics 1994, 13, 148. Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424.
104. (b) Ivin, K. J.; Rooney, J. J.; Stewart, C. D.; Green, M. L. H.; Mahtab, R. J. Chem. Soc., Chem. Commun. 1978, 604. Green, M. L. H. Pure Appl. Chem. 1978, 50, 27. Laverty, D. T.; Rooney, J. J. J. Chem. Soc., Faraday Trans. 1 1983, 79, 869. Brookhart, M.; Green, M. L. H.; Pardy, R. B. A. J. Chem. Soc., Chem. Commun. 1983, 691. Clawson, L.; Soto, J.; Buchwald, S. L.; Steigerwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985, 107, 3377. Piers, W. E.; Bercaw, J. E. J. Am. Chem Soc. 1990, 112, 9406. Krandelat, H.; Brintzinger, H.-H. Angew. Chem. Soc. 1990, 102, 1459; Angew. Chem., Int. Ed. Engl. 1990, 29, 1412. Janiak, B. J. Organomet. Chem. 1993, 452, 63. Barta, N. S.; Kirk, B. A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 8912. Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651, 1996, 118, 9024. Prosenc, M.-H.; Brintzinger, H.-H. Organometallics 1997, 16, 3889. Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. Alelyunas, Y. W.; Gou, Z.; LaPointe, R. E. Jordan, R. F. Organometallics 1993, 12, 544. Alelyunas, Y. W.; Baenziger, N. C.; Bradley, P. K.; Jordan, R. F. Organometallics 1994, 13, 148. Guo, Z.; Swenson, D. C.; Jordan, R. F. Organometallics 1994, 13, 1424.
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