Stoichiometric homo-aldol coupling of acetone, cyclohexanone, and acetophenone by the [(η5-Cp(R))Co] (R = Me5, 1,2,4-tri-tert-butyl) moiety

European Journal of Inorganic Chemistry

Volumn , Issue 4, 2000, Pages 713-718

  Schneider, Jörg J ^a   Wolf, Dirk ^a   Bläser, Dieter ^a   Boese, Roland ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Aldol reactions; C(sp3) H activation; Cobalt; Ketones; Sandwich complexes

Indexed keywords

ACETONE; COBALT COMPOUNDS; TOLUENE;

ACETOPHENONES; ACIDIC PROTON; ACTIVATION STEPS; ALDOL REACTIONS; C(SP3)-H ACTIVATION; CARBONYL CARBON; COBALT COMPLEXES; COBALT COMPLEXES (III); CYCLOHEXANONES; SANDWICH COMPLEXES;

CHEMICAL ACTIVATION;

ACETONE; ACETOPHENONE; BENZOPHENONE; CARBONYL DERIVATIVE; COBALT COMPLEX; CYCLOHEXANONE; TOLUENE;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; STEREOSPECIFICITY; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 0034100307     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(200004)2000:4<713::aid-ejic713>3.0.co;2-a     Document Type: Article

References (48)

1. [1a] G. Dyker, Angew. Chem. 1999, 111, 1808-22; Angew. Chem. Int. Ed. 1999, 38, 1698-1712.
2. [1a] G. Dyker, Angew. Chem. 1999, 111, 1808-22; Angew. Chem. Int. Ed. 1999, 38, 1698-1712.
3. [1b] L. E. Helberg, T. B. Gunnoe, B. C. Brooks, M. Sabat, W. D. Harman, Organometallics 1999, 18, 573-581, and references cited therein.
4. 1 bonding see: F. Delbeq, P. Sautet, J. Am. Chem. Soc. 1992, 114, 2446-2455.
5. [3a] C. P. Lenges, M. Brookhart, P. S. White, Angew. Chem. 1999, 111, 535-538; Angew. Chem. Int. Ed. 1999, 38, 552-555.
6. [3a] C. P. Lenges, M. Brookhart, P. S. White, Angew. Chem. 1999, 111, 535-538; Angew. Chem. Int. Ed. 1999, 38, 552-555.
7. [3b] C. P. Lenges, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 6965-6979.
8. [3c] C. P. Lenges, M. Brookhart, J. Am. Chem. Soc. 1997, 119, 3165-3166.
9. [4a] H. Sitzmann, Chem. Ber. 1990, 123, 2311-2315.
10. [4b] J. J. Schneider, U. Specht, Z. Naturforsch. 1995, 50b, 684-686.
11. [4c] J. Okuda, J. Organomet. Chem. 1990, 385, C39-C42.
12. [4d] H. Sitzmann, G. Wolmershäuser, Z. Naturforsch. 1997, 52b, 398-400.
13. [4c] H. Sitzmann, M. Schär, E. Dorrmann, M. Kelemen, Z. Anorg. Allg. Chem. 1997, 623, 1609-1613.
14. J. J. Schneider, D. Wolf, C. Janiak, O. Heinemann, J. Kuhnigk, C. Krüger, Chem. Eur. J. 1998, 4, 1982-1991.
15. -3. Hydrogen atoms were treated as riding groups with the 1.2 fold (1.5 for methyl groups) isotropic U-values of the equivalent U-values that correspond to the attached C-atoms. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-130276 (5). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
16. J. E. Hill, P. E. Fanwick, I. P. Rothwell, Organometallics 1992, 11, 1771-1773
17. J. A. S. Howell, B. F. G. Johnson, P. L. Josty, J. Lewis, J. Organomet. Chem. 1972, 39, 329-333.
18. [9a] Th. Schmidt, P. Betz, C. Krüger, J. Organomet. Chem. 1991, 402, 97-104.
19. [9b] Th. Schmidt, F. Bienewald, R. Goddard, J. Chem. Soc., Chem. Commun. 1994, 1857-1858.
20. [9c] Th. Schmidt, Habilitation Thesis, University of Cologne 1992.
21. J. J. Schneider, D. Wolf, Z. Naturforsch. 1998, 53b, 1267-1272.
22. M. Brookhart, M. L. H. Green, J. Organomet. Chem. 1983, 250, 395-408.
23. [12a] B. Bosnich, R. W. Barnhart, Organometallics 1995, 14, 4343-4348.
24. [12b] B. Bosnich, D. P. Fairlie, Organometallics 1988, 7, 936-945.
25. [12c] B. Bosnich, D. P. Fairlie, Organometallics 1988, 7, 946-954.
26. [12d] B. Bosnich, J. Whelan, S. H. Bergens, P. Noheda, X. Wang, R. W. Barnhart, Tetrahedron 1994, 50, 4335-4346.
27. [12e] B. Bosnich, X. Wang, Organometallics 1994, 13, 4131-4133.
28. [12f] B. Bosnich, J. Whelan, S. H. Bergens, P. Noheda, X. Wang, R. W. Barnhart, J. Am. Chem. Soc. 1994, 116, 1821-1830.
29. [12g] B. Bosnich, R. W. Barnhart, D. A. Mc. Morran, Inorg. Chim. Acta 1997, 263, 1-9.
30. [13a] R. G. Bergman, A. H. Janowicz, J. Am. Chem. Soc. 1982, 104, 352-354.
31. [13b] R. G. Bergman, A. H. Janowicz, J. Am. Chem. Soc. 1983, 105, 3929-3939.
32. [13c] R. G. Bergman, R. A. Periana, J. Am. Chem. Soc. 1986, 108, 7346-7355.
33. [13d] R. G. Bergman, Science 1984, 223, 902-908.
34. [14a] W. D. Jones, F. J. Feher, Organometallics, 1983, 2, 686-687.
35. [14b] ibid, J. Am. Chem. Soc. 1984, 106, 1650-1663.
36. [14c] W. D. Jones, R. Perutz, R. M. Chin, L. Dong, S. B. Duckett, M. G. Partridge, J. Am. Chem. Soc. 1993, 115, 7685-7695.
37. [15a] W. A. G. Graham, J. K. Hoyano, J. Am. Chem. Soc. 1982, 104, 3723-3725.
38. [15b] W. A. G. Graham, J. K. Hoyano, A. D. Mc Master. J. Am. Chem. Soc. 1983, 105, 7190-7191.
39. C. P. Lenges, M. Brookhart, B. E. Grant, J. Organomet. Chem. 1997, 528, 199-203.
40. [17a] H. Wadepohl, T. Borchert, H. Büchner, H. Pritzkow, Chem. Ber. 1993, 126, 1615-1618.
41. [17b] H. Wadepohl, T. Borchert, H. Pritzkow, Chem. Commun. 1995, 1447-48.
42. [18a] P. E. Siegbahn, J. Am. Chem. Soc. 1996, 118, 1487-1496.
43. [18b] R. G. Bergman, B. C. Moore, A. A. Bengali, J. Am. Chem. Soc. 1995, 117, 3879-3886.
44. E. g. Autorenkollektiv, Organikum, VEB-Verlag der Wissenschaften, 1977.
45. Th. Schmidt, Chem. Ber./Recueil 1997, 130, 453-461.
46. J. J. Schneider, U. Denninger, O. Heinemann, C. Krüger, Angew. Chem. 1995, 107, 631-634; Angew. Chem. Int. Ed. Engl. 1995, 107, 592-594.
47. J. J. Schneider, U. Denninger, O. Heinemann, C. Krüger, Angew. Chem. 1995, 107, 631-634; Angew. Chem. Int. Ed. Engl. 1995, 107, 592-594.
48. J. J. Schneider, N. Czap, D. Spickermann, C. W. Lehmann, F. Laschi, M. Fontani, P. Zanello, J. Organomet Chem. 1999, 590, 7-14.