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.
Similar content being viewed by others
Literature cited
G. G. Skvortsova, V. V. An, L. M An, and V. K. Voronov, Khim. Geterotsikl. Soedin., 1155 (1972).
H. Hopff and H. Lussi, Makromol. Chem., 18/19, 227 (1956).
M. F. Shostakovskii, G. G. Skvortsova, V. V. An, and Yu. A. Mansurov, Khim. Geterotsikl. Soedin., 9 (1969).
V. I. Spektor, Izv. Akad. Nauk Moldav. SSR, 65 (1967); Ref. Zh. Khim., 9Zh262 (1968).
J. H. Brown and J. S. Watt, US Patent No. 2,344,798 (1944); Chem. Abstr., 38, 3665 (1944).
W. Bauer and C. T. Kautter, US Patent No. 2,363,288 (1944); Chem. Abstr., 39, 3178 (1945).
R. L. Adelman, J. Org. Chem., 14, 1057 (1949).
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.
M. F. Shostakovskii and L. I. Komarova, USSR Author's Certificate No. 166,329; Byull. Izobr., No. 22 (1964).
M. F. Shostakovskii, L. I. Komarova, A. Kh. Filippova, and G. V. Ratovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2526 (1967).
G. G. Skvortsova, V. V. An, and Yu. A. Mansurov, USSR Author's Certificate No. 245,133; Byull. Izobr., No. 19 (1969).
H. Hopff and M. A. Osman, Tetrahedron, 24, 2205 (1968).
E. M. Popov and G. I. Kagan, Optika i Spektroskopii, 12, 194 (1961).
K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965).
J. W. Emsley, J. Finney, and L. Sutcliffe, High-Resolution NMR Spectroscopy, Pergamon.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1443–1447, November, 1972.
Rights and permissions
About this article
Cite this article
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00471857