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Article Dans Une Revue New Journal of Chemistry Année : 2021

Oxidative cleavage of cycloalkenes using hydrogen peroxide and a tungsten-based catalyst: towards a complete mechanistic investigation

Résumé

The identification of the intermediates and by-products produced during the oxidative cleavage of cycloalkenes in the presence of H2O2 and a tungsten-based catalyst for the production of dicarboxylic acids has been carried out under various experimental conditions. On the basis of this mechanistic investigation and previous studies from the literature, a complete reaction scheme for the formation of the reaction products and by-products is proposed. In this hypothetical mechanism, the production of a hydroperoxyalcohol intermediate accounts for the two pathways proposed by Noyori and Venturello for the formation of the targeted dicarboxylic acid. In addition, Baeyer–Villiger oxidation of the mono-aldehyde intermediate allows explaining the formation of short chain diacids observed as by-products during the reaction. Hence, the proposed mechanism constitutes a real tool for scientists looking for a better understanding and those heading to set up environmentally friendly conditions for the oxidative cleavage of cycloalkenes.
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Dates et versions

hal-03084823 , version 1 (02-04-2021)

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Tony Cousin, Gregory Chatel, Bruno Andrioletti, Micheline Draye. Oxidative cleavage of cycloalkenes using hydrogen peroxide and a tungsten-based catalyst: towards a complete mechanistic investigation. New Journal of Chemistry, 2021, ⟨10.1039/D0NJ03592K⟩. ⟨hal-03084823⟩
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