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Oxidationsreaktionen am 1-(3,3-Dimethyl-5-norbornen-2-yl)ethanon und ein neuer Zugang zuendo-konfigurierten Isocamphanderivaten

Syntheses in the isocamphane series, XVIII. Oxidation reactions on 1-(3,3-dimethyl-5-norbornene-2-yl)-ethanone and a new approach toendo-configurated isocamphane derivatives

Synthesen in der Isocamphanreihe, 18. Mitt.

  • Organische Chemie Und Biochemie
  • Published:
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Abstract

The synthesis of some new compounds with the isocamphane skeleton obtained by oxidation reactions on the bicyclic ketone3 and its derivatives is described. Some possible routes to theendo-configurated camphenilanic acid (2) have been explored which yet have to be improved to furnish better yields. Separation of mixtures of the acids1 and2 failed. Carboxylation of camphenilone yielded only theexo-configurated isocamphenilanic acid (1).2, however, an important starting material for the preparation ofendo-configurated isocamphane derivatives, can be obtained easily with high yields and sterically pure by oxidation of camphene with H2O2/HCOOH. Thus a cheap, one-step method for the preparation of pure2 even in larger quantities is introduced.

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Authors and Affiliations

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

    Gerhard Buchbauer, Renate Vitek, Margit C. Hirsch, Christina Kurz, Barbara Cech & Eva Maria Vas

Authors
  1. Gerhard Buchbauer
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  2. Renate Vitek
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  3. Margit C. Hirsch
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  4. Christina Kurz
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  5. Barbara Cech
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  6. Eva Maria Vas
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Additional information

Auszugsweise vorgetragen auf der 3. Wissenschaftlichen Tagung der Österreichischen Pharmazeutischen Gesellschaft am 18. Oktober 1982 in Innsbruck.

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Buchbauer, G., Vitek, R., Hirsch, M.C. et al. Oxidationsreaktionen am 1-(3,3-Dimethyl-5-norbornen-2-yl)ethanon und ein neuer Zugang zuendo-konfigurierten Isocamphanderivaten. Monatsh Chem 113, 1433–1450 (1982). https://doi.org/10.1007/BF00808943

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  • DOI: https://doi.org/10.1007/BF00808943

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