Enaminone substituents attached to cyclopentadienes: 3E/3Z stereochemistry of 1-metalla-1,3,5-hexatriene intermediates (M = Cr, W) as a functional criterion for the formation of cyclopentadienes and six-membered heterocycles, respectively

Chemistry - A European Journal

Volumn 7, Issue 3, 2001, Pages 711-720

  Aumann, Rudolf ^a   Göttker Schnetmann, Inigo ^a   Fröhlich, Roland ^a   Saarenketo, Pauli ^a   Holst, Christiane ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Alkynes; C C coupling; Carbene complexes; Chromium; Cyclopentadienyl ligands; Tungsten

Indexed keywords

ALKYNE DERIVATIVE; AZULENE DERIVATIVE; CARBENOID; CHROMIUM; CYCLOPENTADIENE DERIVATIVE; INDENE DERIVATIVE; TUNGSTEN DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CYCLIZATION; ISOMERISM; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035793295     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010202)7:3<711::AID-CHEM711>3.0.CO;2-5     Document Type: Article

References (22)

1. H.-P. Wu, R. Aumann, R. Fröhlich, P. Saarenketo, Chem. Eur. J. 2001, 7, 700-710.
2. For a recent review on (1-alkynyl)carbene complexes see:R. Aumann, H. Nienaber, Adv. Organomet. Chem. 1997, 41, 161-242.
3. For a detailed description of this reaction type see: a) R. Aumann, H. Heinen, M. Dartmann, B. Krebs, Chem. Ber. 1991, 124, 2343-2347;
4. b) R. Aumann, H. Heinen, P. Hinterding, N. Sträter, B. Krebs, Chem. Ber. 1991, 124, 1229-1236.
5. a) R. Aumann, K. Roths, M. Grehl, Synlett 1993, 669-671;
6. b) R. Aumann, M. Kößmeier, K. Roths, R. Fröhlich, 1994, 1041-1044;
7. c) A. G. Meyer, R. Aumann, Synlett 1995, 1011-1013;
8. d) R. Aumann, K. Roths, B. Jasper, R. Fröhlich, Organometallics 1996, 15, 1257-1264;
9. e) R. Aumann, A. G. Meyer, R. Fröhlich, Organometallics 1996, 15, 5018-5027;
10. f) R. Aumann, M. Kößmeier, F. Zippel, Synlett 1997, 621-623;
11. g) R. Aumann, M. Kößmeier, C. Mück-Lichtenfeld, F. Zippel, Eur. J. Org. Chem. 2000, 37-49.
12. For a recent review on 1-metalla-1,3,5-hexatrienes and related compounds see:R. Aumann, Eur. J. Org. Chem. 2000, 17-31.
13. For the selectivity of these reactions see a recent review on "Pyrylium Carbonylmetalates and Related Compounds Derived from (1-Alkynyl)carbene Complexes" by R. Aumann, M. Kößmeier, K. Roths, R. Fröhlich, Tetrahedron 2000, 56, 4935-4949.
14. H.-P. Wu, R. Aumann, R. Fröhlich, B. Wibbeling, Eur. J. Org. Chem. 2000, 1183-1192.
15. D. J. Darensbourg, B. L. Mueller, C. J. Bischoff, S. S. Chojnacki, J. H. Reibenspies, Inorg. Chem. 1991, 30, 2418-2424;
16. D. J. Darensbourg, J. A. Joyce, C. J. Bischoff, J. H. Reibenspies, Inorg. Chem. 1991, 30, 1137-1142.
17. R. Aumann, R. Fröhlich, J. Prigge, O. Meyer, Organometallics 1999, 18, 1369-1380.
18. For the numbering of atoms see corresponding formula b above.
19. Data sets were collected with Enraf-Nonius CAD4 and Nonius KappaCCD diffractometers, the latter equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MoIEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology, 1997, 276, 307-326), absorption correction for CCD data SORTAV (R. H. Blessing, Acta Cryst. 1995, A51, 33-37;
20. R. H. Blessing, J. Appl. Cryst. 1997, 30, 421-426),
21. structure solution SHELXS-97 (G. M. Sheldrick, Acta Cryst. 1990, A46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC-145712(8e), CCDC-145713 (13e), CCDC-145714 (12 h), CCDC-145715 (16e). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ ccdc.cam.ac.uk).
22. For the numbering of atoms see corresponding formula c above.