Oxidative cleavage of cycloalkenes using hydrogen peroxide and a tungsten-based catalyst: towards a complete mechanistic investigation
| Autor: | Bruno Andrioletti, Micheline Draye, Gregory Chatel, Tony Cousin |
|---|---|
| Přispěvatelé: | Laboratoire de Chimie Moléculaire et Environnement (LCME), Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry]), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
tungsten
oxidation chemistry.chemical_element Tungsten 010402 general chemistry 01 natural sciences catalyse Catalysis chemistry.chemical_compound Materials Chemistry [CHIM]Chemical Sciences Hydrogen peroxide chemistry.chemical_classification catalysis 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Reaction scheme tungstène oxydation General Chemistry [CHIM.CATA]Chemical Sciences/Catalysis Combinatorial chemistry 0104 chemical sciences Dicarboxylic acid chemistry Mechanism (philosophy) Oxidative cleavage |
| Zdroj: | New Journal of Chemistry New Journal of Chemistry, Royal Society of Chemistry, 2021, ⟨10.1039/D0NJ03592K⟩ |
| ISSN: | 1144-0546 1369-9261 |
| DOI: | 10.1039/D0NJ03592K⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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