European Journal of Chemistry

Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters



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Jan Zawadiak
Marek Mrzyczek
Tomasz Piotrowski

Abstract

Dibenzoylmethane and six aromatic 1,3-diketones containing a dibenzoylmethane moiety were synthesized from acetophenone and the appropriate ester in crossed-Claisen condensations. The synthesized diketones include derivatives containing carboxyl and ester groups; bis-(1,3-diketones) were also prepared. The absorption of UV radiation of the obtained compounds was investigated in various solvents, and their molar absorption coefficients were calculated. The ratio of tautomers and keto-enol equilibrium constants were calculated using 1H NMR techniques. Aromatic bis-(1,3-diketones) demonstrated strong hyperchromic effects. The keto-enol equilibrium of the investigated compounds is strongly shifted to the enol form, especially in non-polar solvents.

2_3_289-294_800


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Zawadiak, J.; Mrzyczek, M.; Piotrowski, T. Synthesis and Properties of Aromatic 1,3-Diketones and Bis-(1,3-Diketones) Obtained from Acetophenone and Phtalic Acids Esters. Eur. J. Chem. 2011, 2, 289-294.

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