Russian Journal of General Chemistry

, Volume 88, Issue 2, pp 241–250 | Cite as

Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates

  • E. P. Doronina
  • L. M. Pevzner
  • V. A. Polukeev
  • M. L. Petrov


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.


trifluoromethylfuranes methanephosphonates formylation tautomerism Wittig reaction 


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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • E. P. Doronina
    • 1
  • L. M. Pevzner
    • 1
  • V. A. Polukeev
    • 2
  • M. L. Petrov
    • 1
  1. 1.St. Petersburg Institute of Technology (Technical University)St. PetersburgRussia
  2. 2.Institute of Experimental MedicineSt. PetersburgRussia

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