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Chromatographische Enantiomerentrennung, chiroptische Eigenschaften und absolute Chiralität von Pentacyclo [7.4.1.12,7 .01,9 .02,7]pentadeca-3,5,10,12-tetraen-8-on, einem pentacyclischen Cyclopentanonderivat mitC 2-Symmetrie

Chromatographic resolution, chiroptical properties and absolute chirality of pentacyclo[7.4.1.12,7 .01,9 .02,7]pentadeca-3,5,10,12-tetraene-8-one, a pentacyclic cyclopentanone derivative with C2-symmetry (short communication)

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  • Organische Chemie Und Biochemie
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Abstract

The title compound1 was resolved into enantiomers by medium-pressure liquid chromatography on microcrystalline triacetylcellulose in ethanol. After four cycles pure enantiomers were obtained ([α] 20D + and — 330°, resp., in ethanol) and their circular dichroism spectra recorded. From optical comparison with structurally related thujane derivatives and by applying the octant rule, for (—)-1 the chirality (7R, 9R) was deduced.

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Author notes

  1. Harald Schwager

    Present address: Department of Chemistry, University of Berkeley, 94720, CA, U.S.A.

Authors and Affiliations

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

    Axel Meyer & Karl Schlögl

  2. Max-Planck-Institut für Kohlenforschung, D-4300, Mülheim/Ruhr, Bundesrepublik Deutschland

    Harald Schwager

Authors
  1. Axel Meyer
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  2. Karl Schlögl
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  3. Harald Schwager
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Meyer, A., Schlögl, K. & Schwager, H. Chromatographische Enantiomerentrennung, chiroptische Eigenschaften und absolute Chiralität von Pentacyclo [7.4.1.12,7 .01,9 .02,7]pentadeca-3,5,10,12-tetraen-8-on, einem pentacyclischen Cyclopentanonderivat mitC 2-Symmetrie. Monatsh Chem 118, 535–539 (1987). https://doi.org/10.1007/BF00809937

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  • DOI: https://doi.org/10.1007/BF00809937

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