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Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates

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Abstract

Methods of synthesis of 4-functionalyzed (5-trifluoromethylfur-2-yl)methanephosphonates and (5-methyl-2-trifluoromethylfur-3-yl)methanephosphonate are developed. Their formylation with ethyl formate in the presence of sodium foil is studied. Spectral characteristics of tautomers of obtained derivatives of phosphonoacetic aldehyde are evaluated. It is shown that interaction of obtained formyl derivatives with ethoxycarbonylmethylenetriphenylphosphorane regardless of the structure of the furan fragment leads to 4-furylsubstituted alkyl 4-(diethoxyphosphoryl)but-3-enoate, the abnormal product of Wittig reaction.

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Authors and Affiliations

  1. St. Petersburg Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    E. P. Doronina, L. M. Pevzner & M. L. Petrov

  2. Institute of Experimental Medicine, St. Petersburg, Russia

    V. A. Polukeev

Authors
  1. E. P. Doronina
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  2. L. M. Pevzner
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  3. V. A. Polukeev
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  4. M. L. Petrov
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Corresponding author

Correspondence to L. M. Pevzner.

Additional information

Original Russian Text © E.P. Doronina, L.M. Pevzner, V.A. Polukeev, M.L. Petrov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 2, pp. 262–272.

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Doronina, E.P., Pevzner, L.M., Polukeev, V.A. et al. Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates. Russ J Gen Chem 88, 241–250 (2018). https://doi.org/10.1134/S1070363218020093

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  • DOI: https://doi.org/10.1134/S1070363218020093

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