Monatshefte für Chemie / Chemical Monthly

, Volume 114, Issue 5, pp 605–614 | Cite as

Stereochemie planarchiraler Verbindungen, 9. Mitt.

Chromatographische Enantiomerentrennung, chiroptische Eigenschaften und relative Konfigurationen von 1,6-Methano[10]anulenen und 2,7-Methano[10]azaanulenen
  • Karl Schlögl
  • Michael Widhalm
  • Emanuel Vogel
  • Michael Schwamborn
Organische Chemie Und Biochemie

Stereochemistry of planar chiral compounds, IX. Chromatographic separation into enantiomers, chiroptic properties, and relative configurations of 1,6-methano[10]anulenes and 2,7-methano[10]azaanulenes


The two isomeric 1,6-methano[10]anulene carboxylicacid methylesters as well as 2,7-methano[10]azaanulene and several of its methyl, methoxycarbonyl and bromo derivatives have been separated into enantiomers by chromatography on triacetyl cellulose in ethanol; in seven from eleven cases baseline separation was achieved and thereby optically pure enantiomers obtained. The optical rotations and circular dichroism spectra of all anulenes were recorded. From chemical correlations and comparison of the CD spectra relative configurations were deduced; from chiroptical comparison with 2-methyl-1,6-methano[10]anulene of known absolute configuration and on the basis of the justmentioned correlations also absolute chiralities were tentatively proposed for the methano[10]azaanulenes.


Absolute chiralities Circular dichroism Configurational correlation Triacetylcellulose, chromatography on 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    8. Mitt.:Lehner H., Schlögl K., Paulus H., Monatsh. Chem.112, 511 (1981).Google Scholar
  2. 2.
    Vogel E., Roth H. D., Angew. Chem.76, 145 (1964); Int. Ed. (Engl.)3, 228 (1964).Google Scholar
  3. 3.
    Siehe z. B.:Dobler M., Dunitz J., Helv. Chim. Acta48, 1429 (1965).Google Scholar
  4. 4 a.
    Kuffner U.,Schlögl K., Tetrahedron Lett.1971, 1773; bKuffner U.,Schlögl K., Monatsh. Chem.103, 1320 (1972).Google Scholar
  5. 5.
    Schäfer-Ridder M., Wagner A., Schwamborn M., Schreiner H., Devrout E., Vogel E., Angew. Chem.90, 894 (1978); Int. Ed. (Engl.)17, 853 (1978).Google Scholar
  6. 6.
    Zur Synthese von Derivaten von4 siehe:Schwamborn M., Dissertation (Universität Köln) 1980;Vogel E., Pure and Appl. Chem., im Druck.Google Scholar
  7. 7.
    Bauer K., Falk H., Schlögl K., Angew. Chem.81, 150 (1969); Int. Ed. (Engl.)8, 135 (1969).Google Scholar
  8. 8.
    Schlögl K., Widhalm M., Chem. Ber.115, 3042 (1982).Google Scholar
  9. 9.
    Vogel E.,Sombroek J., Tetrahedron Lett.1974, 1627.Google Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  • Karl Schlögl
    • 1
  • Michael Widhalm
    • 1
  • Emanuel Vogel
    • 2
  • Michael Schwamborn
    • 2
  1. 1.Institut für Organische ChemieUniversität WienWienÖsterreich
  2. 2.Institut für Organische ChemieUniversität KölnKölnBundesrepublik Deutschland

Personalised recommendations