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Chemistry of Heterocyclic Compounds

, Volume 12, Issue 4, pp 406–410 | Cite as

Research on two-ring 1-aza compounds

XIII. Synthesis of 3(5)-hydroxymethylpyrrolizidines by catalytic hydrogenation of 5-hydroxymethyl-1,2-dihydropyrrolizines. Determination of the configurations of the reaction products
  • I. M. Skvortsov
  • S. A. Kolesnikov
Article
  • 26 Downloads

Abstract

5-Hydroxymethyl-1,2-dihydropyrrolizines were catalytically hydrogenated to 3(5)-hydroxymethylpyrrolizidines, and the ratios of the isomers in the products of the reaction, which proceeds stereoselectively, were determined. The configuration of the diastereomers was established on the basis of the results of catalytic isomerization, a study of the chromatographic behavior of the isomers on a polar stationary phase, and a discussion of the isomeric composition of the hydrogenation products in the light of the general principles of the stereochemistry of catalytic hydrogenation. trans- and cis-3,8-H-3-Hydroxymethylpyrrolizidine and trans-3,8-H-3-methyl-trans-5,8-H-5-hydroxymethylpyrrolizidine were isolated from the mixtures of isomers. The existence of an intramolecular hydrogen bond in trans-3,8-H-3-hydroxymethyl- and trans-3,8-H-3-methyl-trans-5,8-H-5-hydroxymethylpyrrolizidine was shown by IR spectroscopy.

Keywords

Hydrogenation Spectroscopy Hydrogen Bond Organic Chemistry Stationary Phase 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    I. M. Skvortsov, I. V. Antipova, Yu. A. Pentin, Tran Suan Hoanh, and S. V. Vasil'kovskii, Khim. Geterotsikl. Soedin., No. 8, 1087 (1975).Google Scholar
  2. 2.
    A. A. Ponomarev, I. M. Skvortsov, and A. A. Khorkin, Zh. Obshch. Khim., 33, 2687 (1963).Google Scholar
  3. 3.
    S. A. Kolesnikov, I. M. Skvortsov, and Yu. Yu. Samitov, Zh. Organ. Khim., 7, 1533 (1971).Google Scholar
  4. 4.
    A. I. Kukina, and A. A. Balandin, Practical Manual of Organic Catalysis [in Russian], Moscow (1966), p. 129.Google Scholar
  5. 5.
    N. D. Zelinskii, Collection of Works [in Russian], Vol. 3, Moscow (1955), p. 272.Google Scholar
  6. 6.
    I. M. Skvortsov and V. M. Levin, Khim. Geterotsikl. Soedin., No. 7, 947 (1973).Google Scholar
  7. 7.
    I. M. Skvortsov, V. M. Levin, S. A. Kolesnikov, and I. V. Antipova, in: Problems in Stereochemistry [in Russian], third edition, Izd. Kievsk. Univ. (1973), p. 27.Google Scholar
  8. 8.
    M. T. Pizzorno and S. M. Albonico, J. Org. Chem., 39, 731 (1974).Google Scholar
  9. 9.
    I. M. Skvortsov, I. V. Antipova, and A. A. Ponomarev, Dokl. Akad. Nauk SSSR, 178, 1106 (1968).Google Scholar
  10. 10.
    I. M. Skvortsov and J. A. Elvidge, J. Chem. Soc., B, 1589 (1968).Google Scholar
  11. 11.
    I. M. Skvortosov and I. V. Antipova, in: Heterogeneous Catalysis in: Reactions for the Preparation and Transformation of Heterocyclic Compounds [in Russian], Riga (1971), p. 123.Google Scholar
  12. 12.
    V. G. Berezkin and V. P. Pakhomov, in: Gas Chromatography [in Russian], ninth edition, Moscow (1969). p. 102.Google Scholar
  13. 13.
    A. N. Kost (editor), General Practical Manual of Organic Chemistry [in Russian], Moscow (1965), p. 615.Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • I. M. Skvortsov
    • 1
  • S. A. Kolesnikov
    • 1
  1. 1.N. G. Chernyshevskii Saratov State UniversityRussia

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