The rhodium-catalyzed cyclotetramerization of butadiene: Isolation and structural characterization of an intermediate

Angewandte Chemie - International Edition

Volumn 39, Issue 13, 2000, Pages 2304-2307

  Bosch, Marco ^a   Brookhart, Maurice S ^b   Ilg, Kerstin ^a   Werner, Helmut ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b The University of North Carolina at Chapel Hill   (United States)

Author keywords

Butadienes; Cyclooligomerizations; Rhodium

Indexed keywords

1,3 BUTADIENE; RHODIUM COMPLEX; TETRAMER;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ISOMER; OLIGOMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034601016     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000703)39:13<2304::AID-ANIE2304>3.0.CO;2-V     Document Type: Article

References (31)

1. H. Werner, M. Bosch, C. Hahn, F. Kukla, M. Laubender, M. Manger, M. E. Schneider, B. Weberndörfer, B. Windmüller, J. Chem. Soc. Dalton Trans. 1998, 3549-3558.
2. a) M. E. Schneider, H. Werner, 10th International Symposium on Homogeneous Catalysis, Princeton, 1996;
3. b) M. E. Schneider, PhD thesis, Universität Würzburg, 1997.
4. a) G. Wilke, Angew. Chem. 1988, 100, 189-211; Angew. Chem. Int. Ed. Engl. 1988, 27, 185-206;
5. a) G. Wilke, Angew. Chem. 1988, 100, 189-211; Angew. Chem. Int. Ed. Engl. 1988, 27, 185-206;
6. b) G. Wilke, B. Bogdanovic, P. Hardt, P. Heimbach, W. Keim, M. Kröner, W. Oberkirch, K. Tanaka, E. Steinrücke, D. Walter, H. Zimmermann, Angew. Chem. 1966, 78, 157-172; Angew. Chem. Int. Ed. Engl. 1966, 5, 151-164;
7. b) G. Wilke, B. Bogdanovic, P. Hardt, P. Heimbach, W. Keim, M. Kröner, W. Oberkirch, K. Tanaka, E. Steinrücke, D. Walter, H. Zimmermann, Angew. Chem. 1966, 78, 157- 172; Angew. Chem. Int. Ed. Engl. 1966, 5, 151-164;
8. c) G. Wilke, Angew. Chem. 1963, 75, 10-20; Angew. Chem. Int. Ed. Engl. 1963, 2, 105-115.
9. c) G. Wilke, Angew. Chem. 1963, 75, 10-20; Angew. Chem. Int. Ed. Engl. 1963, 2, 105-115.
10. a) G. Wilke, A. Eckerle in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, Chap. 2.3.6;
11. b) P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Vol. 2, Academic Press, New York, 1975, Chap. 3.
12. M. Bosch, M. Laubender, B. Weberndörfer, H. Werner, Chem. Eur. J. 1999, 5, 2203-2211.
13. R. Benn, B. Büssemeier, S. Holle, P.W. Jolly, R. Mynott, I. Tkatchenko, G. Wilke, J. Organomet. Chem. 1985, 279, 63-86.
14. 2 = 0.0936 (for all 3884 data); data-to-parameter ratio 11.99; residual electron density +0.797/-0.636. All non-hydrogen atoms were refined anisotropically, and a riding model was employed in the refinement of the hydrogen atom positions. The octadienediyl ligand in 6a is disordered and found with an occupancy of 0.69:0.31, it was refined anisotropically with restrains. Crystallographic data (excluding structure factors) for the structure reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139992. 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).
15. a) R. Wiedemann, R. Fleischer, D. Stalke, H. Werner, Organometallics 1997, 16, 866-870;
16. b) H. Werner, M. Schäfer, O. Nürnberg, J. Wolf, Chem. Ber. 1994, 127, 27-38.
17. a) S. Wache, W. A. Herrmann, G. Artus, O. Nuyken, D. Wolf, J. Organomet. Chem. 1995, 491, 181-188;
18. b) J. W. Steed, D. A. Tocher, Polyhedron 1994, 13, 167-173;
19. c) B. Kavanagh, J.W. Steed, D. A. Tocher, J. Chem. Soc. Dalton Trans. 1993, 327-335;
20. d) D. N. Cox, R. Roulet, J. Organomet. Chem. 1988, 342, 87-95;
21. e) D. N. Cox, R. Roulet, Organometallics 1985, 4, 2001-2005;
22. f) A. Colombo, G. Allegra, Acta Crystallogr. Sect. B 1971, 27, 1653.
23. 2 to give 2-ethyl-2,4,9-undecatrien-4-olide, the formation of an octadiene-diylrhodium complex has been postulated: A. Behr, R. He, K.-D. Juszak, C. Krüger, Y.-H. Tsay, Chem. Ber. 1986, 119, 991-1015.
24. 3 ligand is positioned symmetrically with respect to the octadienediyl moiety); L. Perrin, E. Clot, O. Eisenstein, private communication.
25. a) U. M. Dzhemilev, L. Y. Gubaidullin, Zh. Org. Khim 1976, 12, 44-46 [Chem. Abstr. 1976, 84, 121244];
26. a) U. M. Dzhemilev, L. Y. Gubaidullin, Zh. Org. Khim 1976, 12, 44- 46 [Chem. Abstr. 1976, 84, 121244];
27. b) G. A. Tolstikov, U.M. Dzhemilev, L. Y. Gubaidullin, Ivz. Akad. Nauk SSSR Ser. Khim 1975, 2, 487 [Chem. Abstr. 1975, 82, 139467].
28. b) G. A. Tolstikov, U.M. Dzhemilev, L. Y. Gubaidullin, Ivz. Akad. Nauk SSSR Ser. Khim 1975, 2, 487 [Chem. Abstr. 1975, 82, 139467].
29. A. Miyake, H. Kondo, M. Nishino, Angew. Chem. 1971, 83, 851-852; Angew. Chem. Int. Ed. Engl. 1971, 10, 802-803.
30. A. Miyake, H. Kondo, M. Nishino, Angew. Chem. 1971, 83, 851-852; Angew. Chem. Int. Ed. Engl. 1971, 10, 802-803.
31. 1H} NMR data of the anionic ligand are omitted for clarity.