Phosphine-catalyzed dimerization of activated alkenes under ambient and high pressure conditions

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3091-3094

  Jenner, Gérard ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Acrylic compounds; Dimerization; Morita Baylis Hillman reaction; Phosphines; Pressure

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; HYPERBARISM; SYNTHESIS;

EID: 0034701463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00346-4     Document Type: Article

References (13)

1. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062.
2. Hill, J. S.; Isaacs, N. S. Tetrahedron Lett. 1986, 27, 5007-5010.
3. Jenner, G. High Press. Res. 1999, 16, 243-252.
4. Aggarwal, V. K.; Mereu, A. Chem. Commun. 1999, 2311-2312.
5. Van Rozendaal, E. L.; Voss, B. M.; Scheeren, H. W. Tetrahedron 1993, 31, 6931-6936.
6. Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
7. Amri, H.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1989, 30, 7381-7382.
8. Roth, F.; Gygax, P.; Frater, G. Tetrahedron Lett. 1992, 33, 1045-1048.
9. Rafel, S.; Leahy, J. W. J. Org. Chem. 1997, 62, 1521-1522.
10. 3).
11. 2-Methylene glutaro-nitrile and methyl ester could be synthesized via transition metal catalyzed dimerization of acrylonitrile and methyl acrylate, respectively. However, the reactions were not selective (other dimers were also produced) and needed prolonged reaction times. Crotonic derivatives did not react under such conditions. Watanabe, Y.; Takeda, M. Bull. Chem. Soc. Jpn. 1973, 46, 883-887.
12. Hwu, J. R.; Hakimelahi, G. H.; Chou, C. Y. Tetrahedron Lett. 1992, 33, 6469-6472.
13. In contrast with the excellent yields reported in the DBU catalyzed MBH reaction (Ref. 4), the phosphines used in the present work did not catalyze the MBH addition of benzaldehyde to acrylic compounds.