Selective tail-to-tail dimerization of ethyl acrylate catalyzed by dirhodium complexes

Chemistry Letters

Volumn , Issue 1, 1997, Pages 23-24

  Kaneko, Yuichi ^b   Kanke, Tsuyoshi ^b   Kiyooka, Syun Ichi ^b   Isobe, Kiyoshi ^a  

^a Osaka Prefecture University   (Japan)

^b KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031534690     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.23     Document Type: Article

References (20)

1. G. Süss-Fink and G. Meister, Adv. Organomet. Chem., 35, 41 (1993).
2. K. Isobe, S. Okeya, N. J. Meanwell, A. J. Smith, H. Adams, and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1984, 1215.
3. For a recent review of Di-μ-methylene dirhodium complex, see: P. M. Maitlis, J. Organomet. Chem., 506, 239 (1995) and references are cited therein.
4. Y. Kaneko, T. Suzuki, S. Kiyooka, and K. Isobe, submitted for publication.
5. Study of oligomerization of other electron deficient olefinic compounds is now in progress.
6. We also examined the reactions of methyl acrylate and isobutyl acrylate with the dirhodium complexes. Because the effects of the ester parts on yield and selectivity are of minor importance, we only pick out the results of using ethyl acrylate for the catalytic reaction.
7. For reports of acrylate dimerization by metal complex catalysts, see: a) T. Alderson, E. L. Jenner, and V. Lindsey, Jr., J. Am. Chem. Soc., 87, 5638 (1965).
8. b) W. A. Nugent and F. W. Hobbs, Jr., J. Org. Chem., 48, 5364 (1983).
9. c) P. Grenouillet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984).
10. d) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985).
11. e) R. J. McKinney, Organometallics, 5, 1752 (1986).
12. f) G. Oehme and H. Pracejus, J. Organomet. Chem., 320, C56 (1987).
13. g) G. Wilke, Angrew. Chem., Int. Ed. Engl., 27, 185 (1988).
14. h) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Catal., 85, 149 (1993).
15. i) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calablese, J. Am. Chem. Soc., 116, 8038 (1994).
16. 2 on the acrylate dimerization has been reported in mononuclear rhodium complex catalysts, see Ref. 7i.
17. 2.
18. R. F. Jordan, W. E. Dasher, and S. F. Echols, J. Am. Chem. Soc., 108, 1718 (1986).
19. K. Isobe, A. Vázquez de Miguel, P. M. Bailey, S. Okeya, and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1983, 1441.
20. G. J. Sunley, I. M. Saez, and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1992, 2193.