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Mechanistic investigation of the base-promoted cycloselenoetherification of pent-4-en-1-ol

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Abstract

The mechanism of phenylselenoetherification of pent-4-en-1-ol using some bases (pyridine, triethylamine, quinoline, 2,2′-bipyridine) as catalyst was examined through studies of kinetics of the cyclization, by UV-VIS spectrophotometry. It was demonstrated that the intramolecular cyclization is facilitated in the presence of bases caused by the hydrogen bond between base and alkenol’s OH-group. The obtained values for rate constants have shown that the reaction with triethylamine is the fastest one. Quantum chemical calculations (MP2(fc)/6-311+G**//B3LYP/6-311+G**) show, that the transition state of the cyclisation is SN2 like.

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Acknowledgments

This work was funded by the Minister of Science, Technology and Development of the Republic of Serbia (Grant: 142008). We would like to thank Prof. Rudi van Eldik for support and Prof. Tim Clark for hosting this work in the CCC and the Regionales Rechenzentrum Erlangen (RRZE) for a generous allotment of computer time.

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Authors and Affiliations

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

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

  2. Inorganic Chemistry, Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Egerlandstrasse 1, 91058, Erlangen, Germany

    Ralph Puchta

Authors
  1. Marina D. Rvovic
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  2. Vera M. Divac
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  3. Ralph Puchta
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  4. Zorica M. Bugarčić
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Correspondence to Zorica M. Bugarčić.

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Rvovic, M.D., Divac, V.M., Puchta, R. et al. Mechanistic investigation of the base-promoted cycloselenoetherification of pent-4-en-1-ol. J Mol Model 17, 1251–1257 (2011). https://doi.org/10.1007/s00894-010-0824-3

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  • DOI: https://doi.org/10.1007/s00894-010-0824-3

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