Abstract
A new one-step modification of the synthesis of cyclopropane-ring-substituted 2-furylcyclopropanes by the Kishner method from α,β-unsaturated ketones of the furan series is proposed. Disubstituted cyclopropanes are obtained in the form of mixtures of the cis and trans isomers, as proved by the PMR and gas-liquid chromatography data.
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N. M, Kizhner (Kishner), Zh. Russk. Fiz. Khim. Obshchestva, 61, 781 (1929).
D. J. Cram, Fundamentals of the Chemistry of Carbanions [Russian translation], Mir, Moscow (1967), p. 176 [Fundamentals of Carbanion Chemistry, Academic Press (1965)].
Huang-Minlon, J. Am. Chem. Soc., 68, 2487 (1946).
N. I. Shuikin and V. V. Daiber, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 121 (1941).
Yu. K. Yur'ev and D. Eckhardt, Zh. Obshch. Khim., 31, 3274 (1961).
V. A. Slabey, J. Am. Chem. Soc., 76, 3604 (1954).
A. R. Katritzky (editor), Physical Methods in the Chemistry of Heterocyclic Compounds, Academic Press (1963).
A. P. Meshcheryakov, V. G. Glukhovtsev, and N. N. Lyamin, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 10, 1901 (1961).
V. G. Glukhovtsev, S. V. Zakharova, and G. K. Vasilevskaya, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1330 (1964).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1032–1035, August, 1977.
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Zefirova, V.A., Karakhanov, R.A. Synthesis of 2-furylcyclopropanes new modification of the kishner synthesis of cyclopropanes. Chem Heterocycl Compd 13, 828–831 (1977). https://doi.org/10.1007/BF00488900
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DOI: https://doi.org/10.1007/BF00488900