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Synthesis of phosphonic esters containing heterocyclic groups

Communication 6. Reaction of phosphorous esters with 2-furaldehyde, 2-furoic acid, and 2-furanacrylic acid

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Summary

  1. 1.

    Triethyl and triisopropyl phosphites, when reacting with 2-furaldehyde and with benzaldehyde, are partially oxidized to phosphoric esters with formation of 2,2′-vinylenedifuran and stilbene, respectively.

  2. 2.

    When triethyl phosphite reacts with 2-furoic acid and with 2-furanacrylic acid, the ethyl esters of these acids are formed. In the case of 2-furanacrylic acid, not only the formation of a 2-furanacrylic ester occurs, but also the addition of the trialkyl phosphite to 2-furanacrylic acid.

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Literature cited

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    G. Kamai and V. A. Kukhtin, Zhur. Obshch. Khim.27, 2376, 2372 (1957).

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    V. S. Abramov, Doklady Akad. Nauk SSSR95, 991 (1954).

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    F. W. Hoffmann, R. J. Ess, T. C. Simmons, and R. S. Hanzel, J. Am. Chem, Soc.78, 6414 (1956).

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    C. Walling and R. Rabinowitz, J. Am. Chem. Soc.79, 5326 (1957).

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    F. W. Hoffman and H. D. Weiss, J. Am. Chem. Soc.79, 4759 (1957).

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Arbuzov, B.A., Zoroastrova, V.M. Synthesis of phosphonic esters containing heterocyclic groups. Russ Chem Bull 9, 962–965 (1960). https://doi.org/10.1007/BF00903969

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Keywords

  • Ester
  • Ethyl
  • Benzaldehyde
  • Ethyl Ester
  • Stilbene