Skip to main content
SpringerLink
Log in

Stereochemie planarchiraler Verbindungen, 9. Mitt.

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

Chromatographische Enantiomerentrennung, chiroptische Eigenschaften und relative Konfigurationen von 1,6-Methano[10]anulenen und 2,7-Methano[10]azaanulenen

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literatur

  1. 8. Mitt.:Lehner H., Schlögl K., Paulus H., Monatsh. Chem.112, 511 (1981).

    Google Scholar 

  2. Vogel E., Roth H. D., Angew. Chem.76, 145 (1964); Int. Ed. (Engl.)3, 228 (1964).

    Google Scholar 

  3. Siehe z. B.:Dobler M., Dunitz J., Helv. Chim. Acta48, 1429 (1965).

    Google Scholar 

  4. Kuffner U.,Schlögl K., Tetrahedron Lett.1971, 1773; bKuffner U.,Schlögl K., Monatsh. Chem.103, 1320 (1972).

  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. Zur Synthese von Derivaten von4 siehe:Schwamborn M., Dissertation (Universität Köln) 1980;Vogel E., Pure and Appl. Chem., im Druck.

  7. Bauer K., Falk H., Schlögl K., Angew. Chem.81, 150 (1969); Int. Ed. (Engl.)8, 135 (1969).

    Google Scholar 

  8. Schlögl K., Widhalm M., Chem. Ber.115, 3042 (1982).

    Google Scholar 

  9. Vogel E.,Sombroek J., Tetrahedron Lett.1974, 1627.

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Österreich

    Karl Schlögl & Michael Widhalm

  2. Institut für Organische Chemie, Universität Köln, D-5000, Köln, Bundesrepublik Deutschland

    Emanuel Vogel & Michael Schwamborn

Authors
  1. Karl Schlögl
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michael Widhalm
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Emanuel Vogel
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Michael Schwamborn
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Anulen leitet sich vom latein.anulus ab und wird daher hier (wie auch früher)4 im Gegensatz zur allgemeinen Gepflogenheit miteinem n geschrieben.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Schlögl, K., Widhalm, M., Vogel, E. et al. Stereochemie planarchiraler Verbindungen, 9. Mitt.. Monatsh Chem 114, 605–614 (1983). https://doi.org/10.1007/BF00798616

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00798616

Keywords

Search

Navigation