"Dimers" and "trimers" of tetrahydroindenes and hexahydroazulenes, respectively generated from [2-(1-cycloalkenyl)ethynyl]carbene complexes (M = W, Cr) by cascade cyclization/cycloaddition reactions

Chemistry - A European Journal

Volumn 7, Issue 3, 2001, Pages 700-710

  Wu, He Ping ^a   Aumann, Rudolf ^a   Fröhlich, Roland ^a   Saarenketo, Pauli ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Alkynes; C C coupling; Carbene complexes; Cascade reactions; Cyclopentadienyl ligands; Tungsten

Indexed keywords

AZULENE DERIVATIVE; CARBENOID; CYCLOPENTADIENE DERIVATIVE; DIMER; INDENE DERIVATIVE;

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

EID: 0035793278     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010202)7:3<700::AID-CHEM700>3.0.CO;2-D     Document Type: Article

References (25)

1. H.-P. Wu, R. Aumann, S. Venne-Dunker, P. Saarenketo, Eur. J. Org. Chem. 2000, 3463-3473.
2. For a recent review on (1-alkynyl)carbene complexes see: R. Aumann, H. Nienaber, Adv. Organomet. Chem. 1997, 41, 163-242.
3. For a recent review on the preparation of five-membered carbocyclic rings from Fischer carbene complexes see: J. W. Herndon, Tetrahedron 2000, 56, 1257-1280.
4. For a recent review on 1-metalla-1,3,5-hexatrienes and related compounds see: R. Aumann, Eur. J. Org. Chem. 2000, 17-31.
5. R. Aumann, R. Fröhlich, Organometallics 1999, 18, 1369-1380.
6. H. Wu, R. Aumann, R. Fröhlich, Eur. J. Org. Chem. 2000, 19, 1183-1192.
7. H. Wu, R. Aumann, R. Fröhlich, E. Wegelius, P. Saarenketo, Organometallics 2000, 19, 2373-2381.
8. For related studies, in which 1-metalla-1,3,5-hexatrienes were generated by addition of dienes to (1-alkynyl)carbene complexes, see: a) J. Barluenga, F. Aznar, S. Barluenga, M. Fernández, A. Martín, S. García-Granda, A. Pinera-Nicolás, Chem. Eur. J. 1998, 4, 2280-2298;
9. b) J. Barluenga, F. Aznar, M. A. Palomero, S. Barluenga, Org. Lett. 1999, 541.
10. For the numbering of atoms see formula in Experimental Section.
11. For a detailed description of this reaction type see: a) R. Aumann, H. Heinen, M. Dartmann, B. Krebs, Chem. Ber. 1991, 124, 2343-2347;
12. b) R. Aumann, H. Heinen, P. Hinterding, N. Sträter, B. Krebs, Chem. Ber. 1991, 124, 1229-1236.
13. 13C NMR spectra at low temperature (223 K, 600 MHz), but line broadening resulting from rapid interconversion of these compounds is observed at ambient temperature; see also lit. [5].
14. a) R. Aumann, M. Läge, B. Krebs, Chem. Ber. 1994, 127, 731-738;
15. b) R. Aumann, M. Kößmeier, Ch. Mück-Lichtenfeld, F. Zippel, Eur. J. Org. Chem. 2000, 37-49.
16. R. Aumann, B. Hildmann, R. Fröhlich, Organometallics 1998, 17, 1197-1201.
17. R. Aumann, Z. Yu, R. Fröhlich, Organometallics 1998, 17, 2897-2905.
18. Data sets were collected using 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 MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326)
19. absorption correction for CCD data SORTAV (R. H. Blessing, Acta Crystallogr. Sect A 1995, 51, 33-37;
20. R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426)
21. structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 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-145109 (12a), CCDC-145110 (16), and CCDC-145111 (19a). 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 numbering of atoms see formulas of the corresponding acetoxy derivatives a in Experimental Section.
23. a) R. Aumann, B. Jasper, M. Läge, B. Krebs, Organometallics 1994, 13, 3502-3509;
24. b) R. Aumann, B. Jasper, M. Läge, B. Krebs, Organometallics 1994, 13, 3510-3516.
25. For numbering of atoms see formulas 24a and 24′a.