Ultrasound and ionic liquid: An efficient combination to tune the mechanism of alkenes epoxidation

► Olefin epoxidation in MOPyrroNTf 2 by H 2O 2/NaHCO 3/Mn(TPP)OAc under ultrasound. ► Mechanism probably involves an oxo-manganyl intermediate. ► Crucial role played by ultrasound that influence drastically the oxidation process. ► Unique combination of ultrasound activation and ionic liquid. In thi...

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Bibliographic Details
Published in:Ultrasonics sonochemistry 2012-05, Vol.19 (3), p.390-394
Main Authors: Chatel, Gregory, Goux-Henry, Catherine, Kardos, Nathalie, Suptil, Joel, Andrioletti, Bruno, Draye, Micheline
Format: Article
Language:English
Subjects:
Alkenes
Alkenes - chemistry
Alkenes - radiation effects
Catalysis
Chemical Sciences
Epoxidation
Epoxy Compounds - chemistry
Epoxy Compounds - radiation effects
High-Energy Shock Waves
Ionic liquids
Ionic Liquids - chemistry
Ionic Liquids - radiation effects
Mn porphyrin
Organic chemistry
Radiation Dosage
Sonication - methods
Ultrasound
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Summary:► Olefin epoxidation in MOPyrroNTf 2 by H 2O 2/NaHCO 3/Mn(TPP)OAc under ultrasound. ► Mechanism probably involves an oxo-manganyl intermediate. ► Crucial role played by ultrasound that influence drastically the oxidation process. ► Unique combination of ultrasound activation and ionic liquid. In this proof of concept study, the advantageous properties of both H 2O 2/NaHCO 3/imidazole/Mn(TPP)OAc oxidation system and MOPyrroNTf 2 ionic liquid have been combined under ultrasonic irradiation to give an exceptionally favorable environment for Mn(TPP)OAc catalyzed olefin oxidations. The results reveal the crucial role played by the ultrasonic irradiations that influence drastically the oxidation process. In MOPyrroNTf 2 and under ultrasonic irradiation, the mechanism probably involves an oxo-manganyl intermediate at the expense of the classical bicarbonate-activated peroxide route.
ISSN:1350-4177
1873-2828
DOI:10.1016/j.ultsonch.2011.10.007