Structural Characterization of an (8-trans-η4-Butadiene) Group 4 ansa-Metallocene Complex

Organometallics

Volumn 18, Issue 21, 1999, Pages 4459-4461

  Dahlmann, Marc ^a   Erker, Gerhard ^a   Fröhlich, Roland ^a   Meyer, Oliver ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001432320     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990498h     Document Type: Article

References (33)

1. (a) Yasuda, H.; Kajihara, Y.; Mashima, K.; Nagasuna, K.; Lee, K.; Nakamura, A. Organometallics 1982, 7, 388.
2. (b) Erker, G.; Wicher, J.; Engel, K.; Rosenfeldt, F.; Dietrich, W.; Krüger, C. J. Am. Chem. Soc. 1980, 102, 6344. Erker, G.; Wicher, J.; Engel, E.; Krüger, C. Chem, Ber. 1982, 115, 3300.
3. (b) Erker, G.; Wicher, J.; Engel, K.; Rosenfeldt, F.; Dietrich, W.; Krüger, C. J. Am. Chem. Soc. 1980, 102, 6344. Erker, G.; Wicher, J.; Engel, E.; Krüger, C. Chem, Ber. 1982, 115, 3300.
4. For a compilation of examples see for example: Wang, L.-S.; Fettinger, J. C.; Poli, R. J. Am. Chem. Soc. 1997, 119, 4453. Mashima, K.; Fukumoto, H.; Tani, K; Haga, M.; Nakamura, A. Organometallics 1998, 17, 410, and references therein. Strauch, H. C.; Erker, G.; Fröhlich, R. Organometallics 1998, 17, 5746.
5. For a compilation of examples see for example: Wang, L.-S.; Fettinger, J. C.; Poli, R. J. Am. Chem. Soc. 1997, 119, 4453. Mashima, K.; Fukumoto, H.; Tani, K; Haga, M.; Nakamura, A. Organometallics 1998, 17, 410, and references therein. Strauch, H. C.; Erker, G.; Fröhlich, R. Organometallics 1998, 17, 5746.
6. For a compilation of examples see for example: Wang, L.-S.; Fettinger, J. C.; Poli, R. J. Am. Chem. Soc. 1997, 119, 4453. Mashima, K.; Fukumoto, H.; Tani, K; Haga, M.; Nakamura, A. Organometallics 1998, 17, 410, and references therein. Strauch, H. C.; Erker, G.; Fröhlich, R. Organometallics 1998, 17, 5746.
7. Selected examples: Yasuda, H.; Okamoto, T.; Matsuoka, Y.; Nakamura, A.; Kai, Y.; Kanehisa, N.; Kasai, N. Organometallics 1989, 8, 1139. Erker, G.; Sosna, F.; Betz, P., Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564. Erker, G.; Pfaff, R.; Kowalski, D.; Würthwein, E.-U.; Krüger, C.; Goddard, R. J. Org. Chem. 1993, 58, 6771. Reviews: Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212. Erker, G. Angew. Chem. 1989, 101, 411; Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
8. Selected examples: Yasuda, H.; Okamoto, T.; Matsuoka, Y.; Nakamura, A.; Kai, Y.; Kanehisa, N.; Kasai, N. Organometallics 1989, 8, 1139. Erker, G.; Sosna, F.; Betz, P., Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564. Erker, G.; Pfaff, R.; Kowalski, D.; Würthwein, E.-U.; Krüger, C.; Goddard, R. J. Org. Chem. 1993, 58, 6771. Reviews: Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212. Erker, G. Angew. Chem. 1989, 101, 411; Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
9. Selected examples: Yasuda, H.; Okamoto, T.; Matsuoka, Y.; Nakamura, A.; Kai, Y.; Kanehisa, N.; Kasai, N. Organometallics 1989, 8, 1139. Erker, G.; Sosna, F.; Betz, P., Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564. Erker, G.; Pfaff, R.; Kowalski, D.; Würthwein, E.-U.; Krüger, C.; Goddard, R. J. Org. Chem. 1993, 58, 6771. Reviews: Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212. Erker, G. Angew. Chem. 1989, 101, 411; Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
10. Selected examples: Yasuda, H.; Okamoto, T.; Matsuoka, Y.; Nakamura, A.; Kai, Y.; Kanehisa, N.; Kasai, N. Organometallics 1989, 8, 1139. Erker, G.; Sosna, F.; Betz, P., Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564. Erker, G.; Pfaff, R.; Kowalski, D.; Würthwein, E.-U.; Krüger, C.; Goddard, R. J. Org. Chem. 1993, 58, 6771. Reviews: Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212. Erker, G. Angew. Chem. 1989, 101, 411; Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
11. Selected examples: Yasuda, H.; Okamoto, T.; Matsuoka, Y.; Nakamura, A.; Kai, Y.; Kanehisa, N.; Kasai, N. Organometallics 1989, 8, 1139. Erker, G.; Sosna, F.; Betz, P., Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564. Erker, G.; Pfaff, R.; Kowalski, D.; Würthwein, E.-U.; Krüger, C.; Goddard, R. J. Org. Chem. 1993, 58, 6771. Reviews: Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212. Erker, G. Angew. Chem. 1989, 101, 411; Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
12. Selected examples: Yasuda, H.; Okamoto, T.; Matsuoka, Y.; Nakamura, A.; Kai, Y.; Kanehisa, N.; Kasai, N. Organometallics 1989, 8, 1139. Erker, G.; Sosna, F.; Betz, P., Werner, S.; Krüger, C. J. Am. Chem. Soc. 1991, 113, 564. Erker, G.; Pfaff, R.; Kowalski, D.; Würthwein, E.-U.; Krüger, C.; Goddard, R. J. Org. Chem. 1993, 58, 6771. Reviews: Erker, G.; Berlekamp, M.; López, L.; Grehl, M.; Schönecker, B.; Krieg, R. Synthesis 1994, 212. Erker, G. Angew. Chem. 1989, 101, 411; Angew. Chem., Int. Ed. Engl. 1989, 28, 397.
13. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
14. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
15. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
16. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
17. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
18. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
19. Temme, B.; Erker, G.; Karl, J.; Luftmann, H.; Fröhlich, R.; Kotila, S. Angew. Chem. 1995, 107, 1867; Angew. Chem., Int. Ed. Engl. 1995, 34, 1755. Devore, D. D.; Timmers, F. J.; Hasha, D. L.; Rosen, R. K.; Marks, T. J.; Deck, P. A.; Stern, C. L. Organometallics 1995, 14, 3132. Karl, J.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 11165. Pindado, G. J.; Thornton-Pett, M.; Bowkamp, M.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem. 1997, 109, 2457; Angew. Chem., Int. Ed. Engl. 1997, 36, 2358. Karl, J.; Dahlmann, M.; Erker, G.; Bergander, K. J. Am. Chem. Soc. 1998, 120, 5643.
20. Reviews; Erker, G.; Krüger, C.; Müller, G. Adv. Organomet. Chem. 1985, 24, 1. Yasuda, H.; Tatsumi, K.; Nakamura, A. Acc. Chem. Res. 1985, 18, 120. A compilation of references on structurally characterized (s-cis-conjugated diene) group 4 and 5 metal structures is provided with the Supporting Information.
21. Reviews; Erker, G.; Krüger, C.; Müller, G. Adv. Organomet. Chem. 1985, 24, 1. Yasuda, H.; Tatsumi, K.; Nakamura, A. Acc. Chem. Res. 1985, 18, 120. A compilation of references on structurally characterized (s-cis-conjugated diene) group 4 and 5 metal structures is provided with the Supporting Information.
22. Kai, Y.; Kanehisa, N.; Miki, K.; Kasai, N.; Mashima, K.; Nagasuna, K.; Yasuda, H.; Nakamura, A. J. Chem. Soc., Chem. Commun. 1982, 191.
23. Strauch, H. C.; Erker, G.; Fröhlich, R.; Nissinen, M.; Eur. J. Inorg. Chem. 1999, 1453. Sperry, C. K.; Rodriguez, G.; Bazan, G. C. J. Organomet. Chem, 1997, 548, 1.
24. Strauch, H. C.; Erker, G.; Fröhlich, R.; Nissinen, M.; Eur. J. Inorg. Chem. 1999, 1453. Sperry, C. K.; Rodriguez, G.; Bazan, G. C. J. Organomet. Chem, 1997, 548, 1.
25. Mise, T.; Miya, S.; Yamazaki, H. Chem. Lett. 1989, 1853.
26. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 1119-1190.
27. Erker, G.; Engel, K.; Krüger, C.; Chiang, A.-P. Chem. Ber. 1982, 115, 3311.
28. Programs used: (data collection) EXPRESS; Nonius B. V., 1994. (data reduction) Fair, K. MolEN; Enraf Nonius B. V., 1990. (structure solution) Sheldrick, G. M. SHELXS-97. Acta Crystallogr. 1990, A46, 467. (structure refinement) Sheldrick, G. M. SHELXL-97; Universität Göttingen, 1997. (graphics) Brandenburg, K. DIAMOND; Universität Bonn, 1996. Keller, E. SCHAKAL; Universität Freiburg, 1997.
29. Programs used: (data collection) EXPRESS; Nonius B. V., 1994. (data reduction) Fair, K. MolEN; Enraf Nonius B. V., 1990. (structure solution) Sheldrick, G. M. SHELXS-97. Acta Crystallogr. 1990, A46, 467. (structure refinement) Sheldrick, G. M. SHELXL-97; Universität Göttingen, 1997. (graphics) Brandenburg, K. DIAMOND; Universität Bonn, 1996. Keller, E. SCHAKAL; Universität Freiburg, 1997.
30. Programs used: (data collection) EXPRESS; Nonius B. V., 1994. (data reduction) Fair, K. MolEN; Enraf Nonius B. V., 1990. (structure solution) Sheldrick, G. M. SHELXS-97. Acta Crystallogr. 1990, A46, 467. (structure refinement) Sheldrick, G. M. SHELXL-97; Universität Göttingen, 1997. (graphics) Brandenburg, K. DIAMOND; Universität Bonn, 1996. Keller, E. SCHAKAL; Universität Freiburg, 1997.
31. Programs used: (data collection) EXPRESS; Nonius B. V., 1994. (data reduction) Fair, K. MolEN; Enraf Nonius B. V., 1990. (structure solution) Sheldrick, G. M. SHELXS-97. Acta Crystallogr. 1990, A46, 467. (structure refinement) Sheldrick, G. M. SHELXL-97; Universität Göttingen, 1997. (graphics) Brandenburg, K. DIAMOND; Universität Bonn, 1996. Keller, E. SCHAKAL; Universität Freiburg, 1997.
32. Programs used: (data collection) EXPRESS; Nonius B. V., 1994. (data reduction) Fair, K. MolEN; Enraf Nonius B. V., 1990. (structure solution) Sheldrick, G. M. SHELXS-97. Acta Crystallogr. 1990, A46, 467. (structure refinement) Sheldrick, G. M. SHELXL-97; Universität Göttingen, 1997. (graphics) Brandenburg, K. DIAMOND; Universität Bonn, 1996. Keller, E. SCHAKAL; Universität Freiburg, 1997.
33. Programs used: (data collection) EXPRESS; Nonius B. V., 1994. (data reduction) Fair, K. MolEN; Enraf Nonius B. V., 1990. (structure solution) Sheldrick, G. M. SHELXS-97. Acta Crystallogr. 1990, A46, 467. (structure refinement) Sheldrick, G. M. SHELXL-97; Universität Göttingen, 1997. (graphics) Brandenburg, K. DIAMOND; Universität Bonn, 1996. Keller, E. SCHAKAL; Universität Freiburg, 1997.