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Issue 20, 2014
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Inverse solvent effects in the heterogeneous and homogeneous epoxidation of cis-2-heptene with [2-percarboxyethyl]-functionalized silica and meta-chloroperbenzoic acid

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Abstract

The rate constants for the epoxidation of cis-2-heptene with [2-percarboxyethyl]-functionalized silica (1a) and meta-chloroperbenzoic acid (mCPBA) (1b) in different solvents have been determined at temperatures in the −10 to 40 °C range. The heterogeneous epoxidation exhibits a dependence of the reaction rate on solvent polarity opposite to its homogeneous counterpart and anomalous activation parameters in n-hexane, which are interpreted in terms of the surface-promoted solvent structure at the solid–liquid interface. The results show that highly polar solvents can strongly inhibit heterogeneous reactions performed with silica-supported reagents or catalysts.

Graphical abstract: Inverse solvent effects in the heterogeneous and homogeneous epoxidation of cis-2-heptene with [2-percarboxyethyl]-functionalized silica and meta-chloroperbenzoic acid

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Publication details

The article was received on 03 Feb 2014, accepted on 14 Mar 2014 and first published on 14 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00253A
Citation: Org. Biomol. Chem., 2014,12, 3246-3250
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    Inverse solvent effects in the heterogeneous and homogeneous epoxidation of cis-2-heptene with [2-percarboxyethyl]-functionalized silica and meta-chloroperbenzoic acid

    R. Mello, J. T. Sarmiento-Monsalve, D. Vargas-Oviedo, R. Acerete, M. E. González-Núñez and G. Asensio, Org. Biomol. Chem., 2014, 12, 3246
    DOI: 10.1039/C4OB00253A

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