Organic syntheses via transition-metal complexes. 99.1 cyclopentadiene annelation to enolizable cyclic ketones via (1-alkynyl)carbene complexes (M = Cr, W)

Organometallics

Volumn 18, Issue 8, 1999, Pages 1369-1380

  Aumann, Rudolf ^a   Fröhlich, Roland ^a   Prigge, Jörg ^a   Meyer, Oliver ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000921410     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9810394     Document Type: Article

References (23)

1. For part 98 of this series see: Aumann, R.; Kössmeier, M.; Jäntti, A. Synlett 1998, 1120.
2. For recent reviews see: (a) de Meijere, A. Pure Appl. Chem. 1996, 68, 61. (b) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 161.
3. For recent reviews see: (a) de Meijere, A. Pure Appl. Chem. 1996, 68, 61. (b) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 161.
4. (a) Aumann, R.; Roths, K; Grehl, M. Synlett 1993, 669.
5. (b) Aumann, R.; Kössmeier, M.; Roths, K.; Fröhlich, R. Synlett 1994, 1041.
6. (c) Meyer, A. G.; Aumann, R. Synlett 1995, 1011.
7. (d) Aumann, R.; Roths, K.; Jasper, B.; Fröhlich, R. Organometallics 1996, 15, 1257.
8. (e) Aumann, R.; Kössmeier, M.; Zippel, F. Synlett 1997, 621.
9. (f) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018.
10. (a) Aumann, R.; Heinen, H., Hinterding, P.; Sträter, N.; Krebs, B. Chem. Ber. 1991, 124, 1229.
11. (b) Aumann, R.; Heinen, H.; Dartmann, M.; Krebs, B. Chem. Ber. 1991, 124, 2343.
12. Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1998; p 204.
13. (a) Fischer, E. O.; Kreissl, F. R. J. Organomet. Chem. 1972, 35, C47.
14. (b) Fischer, E. O.; Kalder, H. J. J. Organomet. Chem. 1977, 131, 57.
15. (c) Fischer, E. O.; Schubert, U.; Kleine, W.; Fischer, H. Inorg. Synth. 1979, 19, 164.
16. (a) Duetach, M.; Stein, F.; Lackmann, R.; Pohl, E.; Herbst-Inner, R.; de Meijere, A. Chem. Ber. 1992, 125, 2051.
17. (b) Aumann, R.; Hinterding, P. Chem. Ber. 1993, 126, 421.
18. Aumann, R.; Roths, K; Fröhlich, R. Organometallics 1997, 16, 5893.
19. Structural data for a vinylogous carbiminium carbonyltungstate are reported in ref 4b.
20. Aumann, R.; Roths, K.; Kössmeier, M.; Fröhlich, R. J. Organomet. Chem. 1998, 556, 119.
21. Aumann, R.; Jasper, B.; Läge, M.; Krebs, B. Chem. Ber. 1994, 127, 2475.
22. Preparation follows the procedure given in ref 5, but dehydration of the carbinol with phosphoryl chloride/pyridine was carried out at 25 °C, since this reaction was exothermic. Furthermore, the reaction mixture was not hydrolyzed but distilled to give a mixture of 1-ethynylcycloalkene and pyridine as the only volatile products, from which pyridine was extracted by stirring with a small excess of phosphoric acid (ca. 80%) at 20 °C, leaving the 1-ethynylcycloalkene behind in good yields.
23. All data sets were collected with an Enraf-Nonius CAD4/ MACH3 diffractometer, equipped with sealed-tube or rotating-anode generators. Programs used: data reduction MolEN, structure solution SHELXS-86, structure refinement SHELXL-93 and SHELXL-97, graphics (with unsystematical numbering schemes) DIAMOND.