Abstract
The mixture of products formed in the nitration of methyl furan-2-carboxylate in acetic anhydride was separated by means of thin-layer and column chromatography. It was found that products of cis and trans addition of acetyl nitrate to the furan ring — methyl 5-nitro-2-ace-toxy-2,5-dihydrofuran-2-carboxylate and 5-nitro-4-acetoxy-4,5-dihydrofuran-2-carboxylate — and methyl 5-nitrofuran-2-carboxylate are formed in the nitration.
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R. Marquis, Compt. Rend., 137, 520 (1903).
R. Marquis, Ann. Chim. Phys., 4, (8), 196 (1905).
B. T. Freure and J. R. Johnson, J. Amer. Chem. Soc., 53, 1142 (1931).
S. Nishida, T. Sato, and J. Sato, Rep. Sci. Res. Inst. (Japan), 31, 430 (1955).
K. K. Venter, Ya. P. Stradyn', and S. A. Giller, Proceedings of the Conference on Physical Methods for the Investigation of Organic Compounds and Chemical Processes [in Russian], Frunze (1964), p. 20.
K. K. Venter and S. A. Giller, Nitro Compounds. Proceedings of the International Symposium Held at the Polish Academy of Sciences, Warsaw, 18–20 September, 1963. Wydawnictwa Naukowo-Techniczne, Warszawa (1964), p. 71.
V. A. Pestunovich, K. K. Venter, and D. O. Lolya, Izv. Akad. Nauk Latv. SSR, No. 10, 69 (1968).
Ya. A. Éidus, K. K. Venter, and I. V. Zuika, Khim. Geterotsikl. Soedin., 402 (1967).
Ya. A. Eidus, D. O. Lolya, K. K. Venter, and A. K. Grinvalde, Izv. Akad. Nauk Latv. SSR, No. 2, 18 (1970) (1970).
B. B. Greene and K. G. Lewis, Tetrahedron Lett., 4759 (1966).
J. P. Jacobsen, J. T. Nielsen, and K. Schaumburg, Acta Chem. Scand., 25, 2785 (1971).
T. Hiraoka, T. Iwashige, and I. Iwai, Chem. Pharm. Bull., 13, 285 (1965).
Ya. Éidus, A. Ékmane, K. Venter, and S. Giller, Atlas of the Electronic Spectra of 5-Nitrofuran Compounds [in Russian], Zinatne, Riga (1968).
L. Bellamy, Infrared Spectra of Complex Molecules, Methuen (1958).
S. Holland and R. Epsztein, Bull. Soc. Chim. France, 1694 (1971).
S. Holland, F. Mercier, N. Le Goff, and R. Epsztein, Bull. Soc. Chim. France, 4357 (1972).
M. P. Scribe, Compt. Rend., 261, 160 (1965).
V. G. Afrikyan and M. T. Grigoryan, Synthesis of Heterocyclic Compounds [in Russian], Vol. 1 (1956), p. 34.
A. A. Akhrem and A. I. Kuznetsova, Thin-Layer Chromatography [in Russian], Moscow (1964).
K. K. Venter, M. A. Apsite, and D. O. Lolya, Izv. Akad. Nauk Latv. SSR, No. 2, 10 (1970).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 883–889, July, 1975.
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Lolya, D.O., Venter, K.K., Liepin'sh, É.É. et al. Nitration of furan derivatives with acetyl nitrate. Chem Heterocycl Compd 11, 773–778 (1975). https://doi.org/10.1007/BF00497291
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DOI: https://doi.org/10.1007/BF00497291