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Investigations of vinyl esters of the furan series

X. Synthesis and spectral investigation of vinyl esters of furan-2-carboxylic acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The vinyl esters of trans-β-(2-furyl) acrylic acid, furan-2-carboxylic acid, 5-bromofuran2-carboxylic acid, and 5-nitrofuran-2-carboxylic acid were synthesized by the reaction of the corresponding acids with acetylene and vinyl acetate. Mercuric acetate and boron trifluoride etherate were used as catalysts for the transvinylation of acids of the furan series. The structures of the vinyl esters obtained were proved by IR and PMR spectroscopy. The distribution of the π-electron density in the molecules of four of the synthesized vinyl and ethyl esters was studied by means of quantum-chemical calculations by the SCF MO LCAO method (Pople variant) using the Raman and UV absorption spectra.

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Literature cited

  1. G. G. Skvortsova, V. V. An, L. M An, and V. K. Voronov, Khim. Geterotsikl. Soedin., 1155 (1972).

  2. H. Hopff and H. Lussi, Makromol. Chem., 18/19, 227 (1956).

    Google Scholar 

  3. M. F. Shostakovskii, G. G. Skvortsova, V. V. An, and Yu. A. Mansurov, Khim. Geterotsikl. Soedin., 9 (1969).

  4. V. I. Spektor, Izv. Akad. Nauk Moldav. SSR, 65 (1967); Ref. Zh. Khim., 9Zh262 (1968).

  5. J. H. Brown and J. S. Watt, US Patent No. 2,344,798 (1944); Chem. Abstr., 38, 3665 (1944).

  6. W. Bauer and C. T. Kautter, US Patent No. 2,363,288 (1944); Chem. Abstr., 39, 3178 (1945).

  7. R. L. Adelman, J. Org. Chem., 14, 1057 (1949).

    Google Scholar 

  8. A. V. Topchiev, S. V. Zavgorodnii, and Ya. M. Paushkin, Boron Fluoride and Its Compounds as Catalysts in Organic Chemistry [in Russian], Izd. Akad. Nauk SSSR, Moscow (1956), p. 9.

    Google Scholar 

  9. M. F. Shostakovskii and L. I. Komarova, USSR Author's Certificate No. 166,329; Byull. Izobr., No. 22 (1964).

  10. M. F. Shostakovskii, L. I. Komarova, A. Kh. Filippova, and G. V. Ratovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2526 (1967).

  11. G. G. Skvortsova, V. V. An, and Yu. A. Mansurov, USSR Author's Certificate No. 245,133; Byull. Izobr., No. 19 (1969).

  12. H. Hopff and M. A. Osman, Tetrahedron, 24, 2205 (1968).

    Google Scholar 

  13. E. M. Popov and G. I. Kagan, Optika i Spektroskopii, 12, 194 (1961).

    Google Scholar 

  14. K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965).

  15. J. W. Emsley, J. Finney, and L. Sutcliffe, High-Resolution NMR Spectroscopy, Pergamon.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1443–1447, November, 1972.

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Skvortsova, G.G., An, V.V., Mansurov, Y.A. et al. Investigations of vinyl esters of the furan series. Chem Heterocycl Compd 8, 1303–1306 (1972). https://doi.org/10.1007/BF00471857

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  • DOI: https://doi.org/10.1007/BF00471857

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