Volume 29, Issue 39
Heterocyclic Compounds
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ChemInform Abstract: Manganese(III) Acetate Dihydrate Catalyzed Aerobic Epoxidation of Unfunctionalized Olefins in Fluorous Solvents.

K. S. RAVIKUMAR

K. S. RAVIKUMAR

BIOCIS-CNRS, Cent. Etud. Pharm., Univ. Paris-Sud, F-92296 Chatenay-Malabry, Fr.

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F. BARBIER

F. BARBIER

BIOCIS-CNRS, Cent. Etud. Pharm., Univ. Paris-Sud, F-92296 Chatenay-Malabry, Fr.

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J.-P. BEGUE

J.-P. BEGUE

BIOCIS-CNRS, Cent. Etud. Pharm., Univ. Paris-Sud, F-92296 Chatenay-Malabry, Fr.

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D. BONNET-DELPON

D. BONNET-DELPON

BIOCIS-CNRS, Cent. Etud. Pharm., Univ. Paris-Sud, F-92296 Chatenay-Malabry, Fr.

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First published: 19 June 2010

Abstract

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ChemInform Abstract

The results show that the commercially available and inexpensive manganese acetate is a good epoxidation reagent in terms of the yields, regioselectivity and stereodependence. Its effectiveness is comparable to that of other transition metals complexed with expensive ligands. The difference in reactivity of olefins in prefluorinated 2-butyltetrahydrofuran and hexafluoroisopropanol is particularly striking as to be seen in the reactions of (XII) and (XIV) or (XVI), respectively. The latter solvent improves highly the epoxidation of non-reactive terminal olefins. The preparation of epoxides is of interest because they are amongst the most synthetic intermediates for the preparation of natural products and epoxy resins.

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