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

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...

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Bibliographic Details
Published in:New journal of chemistry 2015-01, Vol.39 (7), p.5282-5286
Main Authors: Zawadzki, Przemys aw, Matuszek, Karolina, Czardybon, Wojciech, Chrobok, Anna
Format: Article
Language:English
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Summary: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 NaHCO 3 . 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%. A new method for the synthesis of epoxides in the presence of a peroxy ionic liquid as an oxidising agent and a solvent was developed.
ISSN:1144-0546
1369-9261
DOI:10.1039/c5nj00644a