Abstract
Metathesis of hex-1-ene in ionic liquids catalyzed by WCl6 was studied. The metathesis is preceded by isomerization of hex-1-ene to hex-2-ene, from which the main reaction product, viz., oct-4-ene, is derived. The WCl6-1-butyl-3-methylimidazolium tetrafluoroborate (BMIM·BF4) system efficiently catalyzes metathesis of linear olefin, the ionic liquid serving as the reaction medium by forming a stable homogeneous catalytic system with WCl6. The yields of the metathesis products increase with increasing reaction temperature. The addition of tin-containing promoters leads to a substantial increase in the reaction rate. In the WCl6-BMIM·BF4-SnBu4 system, the selectivity of the formation of oct-4-ene is significantly enhanced.
Similar content being viewed by others
References
Ionic Liquids in Synthesis, Eds T. Welton and P. Wassersheid, Wiley-VCH, 2002, 365 pp.
M. S. Sanford, J. A. Love, and R. H. Grubbs, Organometallics, 2001, 20, 5314.
J. C. Mol and J. A. Moulijn, Adv. Catal., 1975, 131.
R. C. Buijsman, E. van Vuuren, and J. G. Sterreburg, Org. Lett., 2001, 3, 3785.
D. Semeril, H. Olivier Bourbigou, C. Bruneau, and P. H. Dixneuf, Chem. Commun., 2002, 146.
N. Audic, H. Clavier, M. Maudeit, and J.-C. Guillemin, J. Am. Chem. Soc., 2003, 125, 9248.
Q. Yao and Y. Zhang, Angew. Chem., Int. Ed., 2003, 42, 3395.
Eur. Pat. 1035093; Chem. Abstr., 2000, 133, 237853.
Yu. M. Zhorov, Izomerizatsiya olefinov [Isomerization of Olefins], Khimiya, Moscow, 1977, 204 pp. (in Russian).
Y. Chauvin, B. Gilbert, and J. Guibard, J. Chem. Soc., Chem. Commun., 1990, 1715.
Author information
Authors and Affiliations
Additional information
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2094–2097, October, 2004.
Rights and permissions
About this article
Cite this article
Vasnev, A.V., Greish, A.A. & Kustov, L.M. Metathesis of hex-1-ene in ionic liquids catalyzed by WCl6 . Russ Chem Bull 53, 2187–2191 (2004). https://doi.org/10.1007/s11172-005-0096-8
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-005-0096-8