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Issue 7, 2015
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A versatile method of epoxide formation with the support of peroxy ionic liquids

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Abstract

The application of the peroxy ionic liquid, 1-butyl-3-methylimidazolium peroxymonosulphate, as an oxidation agent and a solvent for the synthesis of epoxides was described. The 2.5-molar excess of the peroxy ionic liquid to olefin was applied. The reaction system consisted of 1,1,1-trifluoroacetone as an oxirane precursor, which was used with the molar ratio of 1 : 3 relative to olefin and water solution of NaHCO3. Under these conditions the epoxidation of 4-bromocinnamic acid led to the epoxide formation at the ambient temperature in 30 minutes. Dioxiranes, generated from the peroxy ionic liquid and 1,1,1-trifluoroacetone, demonstrated encouraging potential for the epoxidation of a variety of other olefins: styrene, limonene, stilbene, linalyl acetate and a complex steroid molecule with high yields of final epoxides from 65–98%.

Graphical abstract: A versatile method of epoxide formation with the support of peroxy ionic liquids

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Article information


Submitted
14 Mar 2015
Accepted
30 Apr 2015
First published
01 May 2015

New J. Chem., 2015,39, 5282-5286
Article type
Paper
Author version available

A versatile method of epoxide formation with the support of peroxy ionic liquids

P. Zawadzki, K. Matuszek, W. Czardybon and A. Chrobok, New J. Chem., 2015, 39, 5282
DOI: 10.1039/C5NJ00644A

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