Journal of Molecular Modeling

, Volume 17, Issue 6, pp 1251–1257

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

Authors

  • Marina D. Rvovic
    • Faculty of Science, Department of ChemistryUniversity of Kragujevac
  • Vera M. Divac
    • Faculty of Science, Department of ChemistryUniversity of Kragujevac
  • Ralph Puchta
    • Inorganic Chemistry, Department of Chemistry and PharmacyUniversity of Erlangen-Nürnberg
    • Faculty of Science, Department of ChemistryUniversity of Kragujevac
Original Paper

DOI: 10.1007/s00894-010-0824-3

Cite this article as:
Rvovic, M.D., Divac, V.M., Puchta, R. et al. J Mol Model (2011) 17: 1251. doi:10.1007/s00894-010-0824-3

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.

Keywords

AlcoholsCyclizationKinetics

Copyright information

© Springer-Verlag 2010