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Enol phosphates of phosphorylated derivatives of furylacetic aldehyde and furylpiruvic acid

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Abstract

Phosphorylated derivatives of isomeric furylacetic aldehydes and furylpiruvic acids have been synthesized via formylation and oxalylation of dialkyl (ethoxycarbonylfuryl)methanephosphonates under conditions of the Claisen reaction. 1H, 13C, and 31P NMR spectroscopy studies have shown that the products exist as equilibrium mixtures of the carbonyl compounds and its E- and Z-enol forms in chloroform solutions. Acylation of these substances with diethyl chlorophosphate has yielded the corresponding enol phosphates. Influence of the substituents location in the furan ring on predominance of cis- or trans-configuration has been demonstrated.

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Authors and Affiliations

  1. St. Petersburg State Technological Institute (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    L. M. Pevzner

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  1. L. M. Pevzner
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Correspondence to L. M. Pevzner.

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Original Russian Text © L.M. Pevzner, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 11, pp. 1850–1862.

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Pevzner, L.M. Enol phosphates of phosphorylated derivatives of furylacetic aldehyde and furylpiruvic acid. Russ J Gen Chem 84, 2147–2159 (2014). https://doi.org/10.1134/S1070363214110188

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  • DOI: https://doi.org/10.1134/S1070363214110188

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