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Issue 16, 2013
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Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide

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Abstract

Phosphomolybdic acid (PMA) and phosphotungstic acid (PTA) efficiently catalyze the addition of H2O2 to β-diketones to form bridged 1,2,4,5-tetraoxanes. These reactions are not accompanied by the formation of monocyclic peroxides containing hydroxy and hydroperoxide groups or polymeric peroxides. The use of these catalysts made it possible to obtain bridged tetraoxanes from easily oxidizable benzoylacetone derivatives and α-unsubstituted β-diketones. The syntheses are scaled up to ten grams. The resulting peroxides can be easily isolated from the reaction mixture by column chromatography. The yield of tetraoxanes depends on the structure of β-diketone and varies from 12 to 83%. NMR monitoring of two bridged 1,2,4,5-tetraoxanes synthesis was carried out.

Graphical abstract: Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide

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Publication details

The article was received on 17 Nov 2012, accepted on 12 Feb 2013 and first published on 14 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB27239G
Org. Biomol. Chem., 2013,11, 2613-2623

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    Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide

    A. O. Terent'ev, I. A. Yaremenko, V. A. Vil’, I. K. Moiseev, S. A. Kon'kov, V. M. Dembitsky, D. O. Levitsky and G. I. Nikishin, Org. Biomol. Chem., 2013, 11, 2613
    DOI: 10.1039/C3OB27239G

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