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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
Article

Abstract

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.

Keywords

Hydrogenation Organic Chemistry Trans Isomer Catalytic Hydrogenation Considerable Percentage 
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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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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