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Manganese(II)-Induced Oxidation of Limonene by Dioxygen

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Abstract

Manganese(II) complexes {[MnII(bpy)2 2+]MeCN} in acetonitrile activate dioxygen for the oxidation of limonene to produce mainly carvone, carveol, limonene oxide, and perillaldehyde. The reaction efficiencies after 24 h reaction time are approximately 5-times higher than those obtained for analogous iron(II) complexes. However, the 5 h long induction period is observed for the common conditions of the reaction. The simultaneous presence of the catalyst, dioxygen and the substrate is necessary for the active species to be formed. When t-BuOOH is present in the reaction mixture, the induction period does not appear. In contrast, the replacement of t-BuOOH by HOOH completely inhibits the reaction. We have proposed a putative mechanism in which a manganese(IV)–hydroperoxo adduct with incorporated substrate is formed during the induction period and it becomes an active catalyst for limonene oxidation.

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Authors and Affiliations

  1. Faculty of Chemistry, Rzeszów University of Technology, 35-959, Rzeszów, Poland

    Anna Szczepanik & Andrzej Sobkowiak

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  1. Anna Szczepanik
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  2. Andrzej Sobkowiak
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Correspondence to Andrzej Sobkowiak.

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Szczepanik, A., Sobkowiak, A. Manganese(II)-Induced Oxidation of Limonene by Dioxygen. Catal Lett 126, 261–267 (2008). https://doi.org/10.1007/s10562-008-9617-z

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  • DOI: https://doi.org/10.1007/s10562-008-9617-z

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