Chemistry of Heterocyclic Compounds

, Volume 11, Issue 8, pp 949–955 | Cite as

Research on 1-azabicyclic compounds

XII. Synthesis, separation, and stereochemistry of epimeric 3-tert-butylpyrrolizidines
  • I. M. Skvortsov
  • I. V. Antipova
  • Yu. A. Pentin
  • Tran Suan Khoan'
  • S. V. Vasil'kovskii


1-(2-Furyl)-3-amino-4,4-dimethylpentane was used to obtain 3-tert-butyl-1,2-dihydropyrrolizine, the catalytic hydrogenation of which over Rh/Al2O3 at room temperature gives a mixture of cis- and trans-3,8-H-3-ter-butylpyrrolizidines with predominance of the cis isomer, whereas hydrogenation at 90–100 °C gives a mixture containing the trans isomer as the principal component. The three-dimensional structures of the isomers follow from data on the catalytic hydrogenation and isomerization and the IR, Raman, and PME spectra. A considerable percentage of the trans-fused form is characteristic for cis-3,8-H-3-tert-butylpyrrolizidine.


Hydrogenation Organic Chemistry Trans Isomer Catalytic Hydrogenation Considerable Percentage 
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Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • I. M. Skvortsov
    • 1
    • 2
  • I. V. Antipova
    • 1
    • 2
  • Yu. A. Pentin
    • 1
    • 2
  • Tran Suan Khoan'
    • 1
    • 2
  • S. V. Vasil'kovskii
    • 1
    • 2
  1. 1.N. G. Chernyshevskii Saratov State UniversityUSSR
  2. 2.M. V. Lomonosov Moscow State UniversityUSSR

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