Novel and Efficient Syntheses of Bis(η5-tetrahydroindenyl) Dichlorides of Titanium, Zirconium and Hafnium

Synlett

Volumn 1996, Issue 6, 1996, Pages 563-564

  Yang, Qing ^a   Jensen, Michael D ^a  

^a UNIVERSITY OF NORTH DAKOTA   (United States)

Author keywords

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Indexed keywords

EID: 0010533153     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5495     Document Type: Article

References (29)

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2. Samuel, E.; Setton, R. J. Organomet. Chem. 1965, 4, 156.
3. Samuel, E.; Rausch, M. D. J. Am. Chem. Soc. 1973, 95, 6263.
4. (a) Spaleck, W.; Antberg, M.; Rohrmann, J.; Winter, A.; Bachmann, B.; Kiprof, P.; Behm, J.; Herrmann, W. A. Angew. Chem. Int. Ed. Engl. 1992, 31, 1347;
5. (b) Kaminsky, W.; Brintzinger, H. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 507.
6. For typical examples see: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869; (c) Erker, G.; Mollenkopf, C.; Grehl, M.; Fröhlich, R.; Krüger, C.; Noe, R.; Riedel, M. Organometallics 1994, 13, 1950; (d) Halterman, R. L.; Ramsey, T. L. . Organometallics 1993, 12, 2879 (e) Ellis, W. W.; Hollis, T. K.; Odenkirk, W.; Whelan, J.; Ostrander, R.; Rheingold, A. L.; Bosnich, B. Organometallics 1993, 12, 4391; (f) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732
7. For typical examples see: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869; (c) Erker, G.; Mollenkopf, C.; Grehl, M.; Fröhlich, R.; Krüger, C.; Noe, R.; Riedel, M. Organometallics 1994, 13, 1950; (d) Halterman, R. L.; Ramsey, T. L. . Organometallics 1993, 12, 2879 (e) Ellis, W. W.; Hollis, T. K.; Odenkirk, W.; Whelan, J.; Ostrander, R.; Rheingold, A. L.; Bosnich, B. Organometallics 1993, 12, 4391; (f) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732
8. For typical examples see: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869; (c) Erker, G.; Mollenkopf, C.; Grehl, M.; Fröhlich, R.; Krüger, C.; Noe, R.; Riedel, M. Organometallics 1994, 13, 1950; (d) Halterman, R. L.; Ramsey, T. L. . Organometallics 1993, 12, 2879 (e) Ellis, W. W.; Hollis, T. K.; Odenkirk, W.; Whelan, J.; Ostrander, R.; Rheingold, A. L.; Bosnich, B. Organometallics 1993, 12, 4391; (f) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732
9. For typical examples see: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869; (c) Erker, G.; Mollenkopf, C.; Grehl, M.; Fröhlich, R.; Krüger, C.; Noe, R.; Riedel, M. Organometallics 1994, 13, 1950; (d) Halterman, R. L.; Ramsey, T. L. . Organometallics 1993, 12, 2879 (e) Ellis, W. W.; Hollis, T. K.; Odenkirk, W.; Whelan, J.; Ostrander, R.; Rheingold, A. L.; Bosnich, B. Organometallics 1993, 12, 4391; (f) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732
10. For typical examples see: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869; (c) Erker, G.; Mollenkopf, C.; Grehl, M.; Fröhlich, R.; Krüger, C.; Noe, R.; Riedel, M. Organometallics 1994, 13, 1950; (d) Halterman, R. L.; Ramsey, T. L. . Organometallics 1993, 12, 2879 (e) Ellis, W. W.; Hollis, T. K.; Odenkirk, W.; Whelan, J.; Ostrander, R.; Rheingold, A. L.; Bosnich, B. Organometallics 1993, 12, 4391; (f) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732
11. For typical examples see: (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233; (b) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869; (c) Erker, G.; Mollenkopf, C.; Grehl, M.; Fröhlich, R.; Krüger, C.; Noe, R.; Riedel, M. Organometallics 1994, 13, 1950; (d) Halterman, R. L.; Ramsey, T. L. . Organometallics 1993, 12, 2879 (e) Ellis, W. W.; Hollis, T. K.; Odenkirk, W.; Whelan, J.; Ostrander, R.; Rheingold, A. L.; Bosnich, B. Organometallics 1993, 12, 4391; (f) Hitchcock, S. R.; Situ, J. J.; Covel, J. A.; Olmstead, M. M.; Nantz, M. H. Organometallics 1995, 14, 3732
12. (a) Wailes, P. C.; Coutts, R. S. P.; Weigold, H. Organometallic Chemistry of Titanium, Zirconium, and Hafnium; Academic Press: New York, 1974; p 117;
13. (b) Piemontesi, F.; Camurati, I.; Resconi, L.; Balboni, D.; Sironi, A.; Moret, M.; Ziegler, R.; Piccolrovazzi, N. Organometallics 1995, 14, 1256;
14. (c) Yang, Q.; Jensen, M. D. Synlett 1996, 2, 147.
15. Samuel, E.; Rausch, M. D. J. Am. Chem. Soc. 1973, 95, 6263.
16. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
17. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
18. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
19. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
20. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
21. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
22. For examples of the synthesis of ansa-tetrahydroindenyl Ti and Zr complexes, see; (a) Halterman, R. L.; Ramsey Organometallics 1993, 12, 2879; (b) Erker, G.; Psiorz, C.; Frölich, R. Z. Naturforsch. 1995, 50b, 469; (c) Halterman, R. L.; Ramsey, T. M.; Pailes, N. A.; Khan, M. A. J. Organomet. Chem. 1995, 497, 43. For the synthesis of optically active titanocene and zirconocene complexes, see : (d) Paquette, L. A.; Sivik, M. R.; Bzowej, E. I.; Stanton, K. J. Organometallics, 1995, 14, 4865. For examples of tetrahydroindenyl complexes of later transition metals and lanthanides, see: (e) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorganic Chem. 1976, 15, 1381; (f) Zhang, R.; Tsutsui, M. Youji Huaxue, 1982, 5, 350; (g) Austin, R. N.; Clark, T. J.; Dickson, T. E.; Killian, C. M.; Nile, T. A.; Schabacker, D. J.; McPhail, A. T. J. Organomet. Chem. 1995, 491, 11.
23. For the use of this strategy in the preparation of chiral complexes, see: (a) Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E.; Bläser, D.; Boese, R. J. Am. Chem. Soc. 1987, 109, 8105; (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1989, 30, 3513; (c) Chen, Z.; Halterman, R. L. Synlett 1990, 1, 103; (d) Colletti, S. L.; Halterman, R. L. Organometallics 1991, 10, 3438; (e) Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449. For a related review, see: Halterman, R. L. Chem. Rev. 1992, 92, 965.
24. For the use of this strategy in the preparation of chiral complexes, see: (a) Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E.; Bläser, D.; Boese, R. J. Am. Chem. Soc. 1987, 109, 8105; (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1989, 30, 3513; (c) Chen, Z.; Halterman, R. L. Synlett 1990, 1, 103; (d) Colletti, S. L.; Halterman, R. L. Organometallics 1991, 10, 3438; (e) Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449. For a related review, see: Halterman, R. L. Chem. Rev. 1992, 92, 965.
25. For the use of this strategy in the preparation of chiral complexes, see: (a) Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E.; Bläser, D.; Boese, R. J. Am. Chem. Soc. 1987, 109, 8105; (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1989, 30, 3513; (c) Chen, Z.; Halterman, R. L. Synlett 1990, 1, 103; (d) Colletti, S. L.; Halterman, R. L. Organometallics 1991, 10, 3438; (e) Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449. For a related review, see: Halterman, R. L. Chem. Rev. 1992, 92, 965.
26. For the use of this strategy in the preparation of chiral complexes, see: (a) Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E.; Bläser, D.; Boese, R. J. Am. Chem. Soc. 1987, 109, 8105; (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1989, 30, 3513; (c) Chen, Z.; Halterman, R. L. Synlett 1990, 1, 103; (d) Colletti, S. L.; Halterman, R. L. Organometallics 1991, 10, 3438; (e) Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449. For a related review, see: Halterman, R. L. Chem. Rev. 1992, 92, 965.
27. For the use of this strategy in the preparation of chiral complexes, see: (a) Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E.; Bläser, D.; Boese, R. J. Am. Chem. Soc. 1987, 109, 8105; (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1989, 30, 3513; (c) Chen, Z.; Halterman, R. L. Synlett 1990, 1, 103; (d) Colletti, S. L.; Halterman, R. L. Organometallics 1991, 10, 3438; (e) Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449. For a related review, see: Halterman, R. L. Chem. Rev. 1992, 92, 965.
28. For the use of this strategy in the preparation of chiral complexes, see: (a) Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E.; Bläser, D.; Boese, R. J. Am. Chem. Soc. 1987, 109, 8105; (b) Colletti, S. L.; Halterman, R. L. Tetrahedron Lett. 1989, 30, 3513; (c) Chen, Z.; Halterman, R. L. Synlett 1990, 1, 103; (d) Colletti, S. L.; Halterman, R. L. Organometallics 1991, 10, 3438; (e) Chen, Z.; Eriks, K.; Halterman, R. L. Organometallics 1991, 10, 3449. For a related review, see: Halterman, R. L. Chem. Rev. 1992, 92, 965.
29. Mironov, V. A.; Ivanov, A. P.; Kimelfeld, Y. M.; Petrovskaya, L. I.; Akhrem, A. A. Tetrahedron Lett. 1969, 39, 3347.