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Olefin epoxidation with H2O2 in the presence of Mn(II) dicarboxylate coordination polymer catalysts

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Abstract

The Mn(II) dicarboxylate coordination polymers [Mn(μ-terephthalate)(H2O)2] n , [Mn(μ-oxalate)(H2O)2] n , and [Mn(μ-d-(−)-tartrate)] n were prepared in water and characterized by FT-IR spectroscopy and CHN analysis. Particles of the terephthalate catalyst were also synthesized, by reaction of terephthalic acid and MnCl2·4H2O by a sonochemical method. The catalytic potential of these coordination polymers as slow-release sources of catalytically active Mn species was tested in the oxidation of cyclooctene to its epoxide in acetonitrile, using hydrogen peroxide as oxygen source. For the terephthalate species the catalytic activity was found to increase with increasing dielectric constant and dipole moment of the solvent (being highest in acetonitrile), with reaction temperature to a maximum at 60 °C, and with an imidazole co-catalyst (highest activity found for a imidazole-to-catalyst molar ratio of 20:1). Good activity with more than 64% conversion in 24 h was obtained for epoxidation of cyclooctene and cyclohexene, whereas low yields only were obtained from aryl-substituted olefins. Some exo versus endo regioselectivity was found for norbornene.

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Acknowledgments

We are grateful to the Zanjan and Tarbiat Modares Universities for financial support of this study, and for DFG grant Ja466/14-1/2.

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Authors and Affiliations

  1. Department of Chemistry, Zanjan University, 45195-313, Zanjan, Islamic Republic of Iran

    Hassan Hosseini Monfared & Azar Mohajeri

  2. Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Islamic Republic of Iran

    Ali Morsali

  3. Institut für Anorganische und Analytische Chemie, Universität Freiburg, Albertstr. 21, 79104, Freiburg, Germany

    Christoph Janiak

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  1. Hassan Hosseini Monfared
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Correspondence to Hassan Hosseini Monfared.

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Hosseini Monfared, H., Mohajeri, A., Morsali, A. et al. Olefin epoxidation with H2O2 in the presence of Mn(II) dicarboxylate coordination polymer catalysts. Monatsh Chem 140, 1437–1445 (2009). https://doi.org/10.1007/s00706-009-0215-6

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