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

PubMed
Authors: Rvovic MD, Divac VM, Puchta R, Bugarčić ZM

Year

2011

Paper ID

12312

Status

Peer-reviewed

Abstract Read

~2 min

Abstract Words

93

Citations

17

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 S(N)2 like.

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  • 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...

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References & Citation Signals

[1] DOI https://doi.org/10.1007/s00894-010-0824-3 [2] Publisher https://pubmed.ncbi.nlm.nih.gov/20711793/

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External citation index: OpenAlex citation signal • updated 2026-06-18 02:34:33

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