Abstract
Mixtures of isomeric 5-, 6-, and 7-carbethoxymethyl-1,2-dihydropyrrolizines were obtained by reaction of 1,2-dihydropyrrolizines with ethyl diazoacetate. The effect of the position of the alkyl groups in the two-membered ring on the ratio of isomers in the reaction products is demonstrated. A method for the isolation of 5-carbethoxymethyl-1,2-dihydropyrrolizines from the mixtures of isomers based on the difference in their reactivities in diazo coupling is described. The preferred conformations of the two-membered rings in the 5-carbethoxymethyl-1,2-dihydropyrrolizines are judged from the PMR spectral data.
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I. M. Skvortsov and I. V. Antipova, Khim. Geterotsikl. Soedin., No. 8, 1060 (1976).
I. M. Skvortsov and S. A. Kolesnikov, in: News in the Chemistry of Carbenes (Material from the First All-Union Conference on the Chemistry of Carbenes and Their Analogs) [in Russian], Moscow (1973), p. 116.
I. M. Skvortsov and S. A. Kolesnikov, Khim. Geterotsikl. Soedin., No. 4, 572 (1971).
E. C. Kleiderer and R. Adams, J. Am. Chem. Soc., 55, 4219 (1933).
A. R. Katritzky (editor), Physical Methods in the Chemistry of Heterocyclic Compounds, Academic Press (1963).
A. Kreutzberger and P. A. Kalter, J. Phys. Chem., 65, 624 (1961).
U. Eisner and R. L. Erskine, J. Chem. Soc., No. 3, 971 (1958).
A. F. Mironov, L. D. Miroshnichenko, R. P. Evstigneeva, and N. A. Preobrazhenskii, Khim. Geterotsikl. Soedin., No. 1, 74 (1965).
R. A. Jones, Spectrochim. Acta, 23A, 2211 (1967).
K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 54.
A. A. Ponomarev, I. M. Skvortsov, and V. M. Levin, Khim. Geterotsikl. Soedin., No. 10, 1339 (1970).
S. A. Kolesnikov, I. M. Skvortsov, and Yu. Yu. Samitov, Zh. Org. Khim., 7, 1533 (1971).
W. Flitsh and H. Peters, Tetrahedron Lett., No. 12, 1475 (1968).
R. L. Hinman and S. Theodoropulos, J. Org. Chem., 28, 3052 (1963).
R. A. Jones, T. McL. Spotswood, and P. Cheychit, Tetrahedron, 23, 4469 (1967).
Nuclear Magnetic Resonance for Organic Chemists, London-New York (1967), p. 188.
W. Kirmse, Carbene Chemistry, Academic Press, New York (1964).
H. Fischer and H. Ort, The Chemistry of Pyrrole [Russian translation], Leningrad (1937), p. 143.
A. Treibs and G. Fritz, Ann., 611, 162 (1958).
G. M. Badger, R. L. Harris, and R. A. Jones, Austr. J. Chem., 17, 1022 (1964).
S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Suchkova, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 3, 331 (1976).
V. I. Bogomolov and Kh. M. Minachev, in: Molecular Chromatography [in Russian], Nauka (1964), p. 10.
Organic Syntheses [Russian translation], Collective Vol. 3, Inostr. Lit., Moscow (1952), p. 512.
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See [1] for communication XV.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1090–1096, August, 1977.
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Skvortsov, I.M., Kolesnikov, S.A., Samitov, Y.Y. et al. Research on 1-aza two-ring systems. Chem Heterocycl Compd 13, 877–883 (1977). https://doi.org/10.1007/BF00488915
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DOI: https://doi.org/10.1007/BF00488915