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Evaluation of some 5-pyrazolone-based copper(II) complexes as catalysts for the oxidation of trans-stilbene

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Chemistry of Heterocyclic Compounds Aims and scope

The catalytic properties of the azo- and bisazo-5-pyrazolone-based three copper(II) complexes have been studied. Heating under reflux with or without ultrasonic irradiation was applied for the different equivalent amounts of three copper(II) catalysts (0.6 and 1.0 mol %) in ethyl acetate. It has been shown that all pyrazolone-based copper(II) complexes are active for catalytic oxidation of trans-stilbene in the presence of tert-butyl hydroperoxide as the oxidant, providing high selectivity and good conversion values. Heating was applied to the different solvents: chloroform, tetrahydrofuran, N,N-dimethylformamide, and dioxane. All catalysts can be safely used near to the boiling point of the oxidant without decomposition and the efficacy of ethyl acetate under conventional heating and heating–ultrasonic conditions has been determined. Heating–ultrasonic conditions and 1.0 mol % of catalysts gave higher conversion than conventional heating and 0.6 mol % of catalysts. A mechanism is proposed for the catalytic oxidation of trans-stilbene with tert-butyl hydroperoxide.

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The author is thankful to ODU/BAP, Ordu University, Scientific Research Projects Coordination Department (Project number AR-1235) and TUBITAK, the Scientific and Technological Research Council of Turkey (Project number 110T549) for financial support, and to the Central Research Laboratory of Ordu University for GC-MS analysis.

A part of this work was presented by E. Bagdatli at the conference “Trans Mediterranean Colloquium on Heterocyclic Chemistry (TRAMECH-VIII)”, November 11–15, 2015, Antalya, Turkey.

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  1. Chemistry Department, Faculty of Arts and Sciences, Ordu University, 52200, Merkez Ordu, Turkey

    Emine Bagdatli

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  1. Emine Bagdatli
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Correspondence to Emine Bagdatli.

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Supplementary information file, containing GC chromatograms and mass spectra of the reaction mixture in experiments and UV-Vis spectra according to the reaction time determination, is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 861–866

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Bagdatli, E. Evaluation of some 5-pyrazolone-based copper(II) complexes as catalysts for the oxidation of trans-stilbene. Chem Heterocycl Comp 53, 861–866 (2017). https://doi.org/10.1007/s10593-017-2151-4

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  • DOI: https://doi.org/10.1007/s10593-017-2151-4

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