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Kinetic investigation in the formation of 2,2,5-trisubstituted tetrahydrofurans by catalyzed phenylselenoetherification of some terpenic alcohols

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Abstract

The mechanism of the phenylselenoetherification of some naturally occurring alcohols linalool and nerolidol in the presence of some bases (piperidine, pyridine, triethylamine, quinoline) as catalysts was examined through the kinetic study of the cyclization under pseudo-first order conditions by UV–Vis spectrophotometry. It was demonstrated that the intramolecular cyclization is facilitated in the presence of some bases caused by the hydrogen bond between base and OH-group of the alkenol. The obtained values for the rate constants show that there is a good agreement between those constants and the basicity of the catalyst. The fastest reaction is the one using the strongest base (piperidine) and the smallest rate constant corresponded to the use of the weakest base (quinoline).

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Acknowledgments

This work was funded by the Ministry of Education and Science of the Republic of Serbia (Grant: 172011).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000, Kragujevac, Serbia

    Vera M. Divac, Marina D. Rvović & Zorica M. Bugarčić

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  1. Vera M. Divac
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  2. Marina D. Rvović
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  3. Zorica M. Bugarčić
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Correspondence to Vera M. Divac.

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Divac, V.M., Rvović, M.D. & Bugarčić, Z.M. Kinetic investigation in the formation of 2,2,5-trisubstituted tetrahydrofurans by catalyzed phenylselenoetherification of some terpenic alcohols. Reac Kinet Mech Cat 110, 309–316 (2013). https://doi.org/10.1007/s11144-013-0620-z

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