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Bishomocamphenilon, Bishomocamphen und Bishomocamphenilansäure: Synthesen in der Isocamphanreihe, 32. Mitt.

Bishomocamphenilone, bishomocamphene and bishomocamphenilanic acid: Syntheses in the isocamphane series, XXXII

  • Organische Chemie Und Biochemie
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Summary

Syntheses of the title compounds are described and their olfactive properties discussed. Bishomocamphenilone (2) has been prepared by a Diels-Alder reaction of acrylonitril and cycloheptadiene-1,3 via the bicyclonitril5 which upon geminal chlorination and alkaline oxidation furnished the bishomonorbornanone9 which then could be transformed into2 by twofold methylation.14 has been prepared by action ofMeLi upon2 and bishomocamphene by dehydration of14. Hydroboration of this olefine3 yielded the alcohol15, which could be oxidized to the corresponding aldehyde13 and bishomocamphenilanic acid (4). The configurations of all new compounds has been ascertained.

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Authors and Affiliations

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

    Gerhard Buchbauer, Helmut Spreitzer, Friederike Zechmeister-Machhart & Martha Pleßl

Authors
  1. Gerhard Buchbauer
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  2. Helmut Spreitzer
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  3. Friederike Zechmeister-Machhart
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  4. Martha Pleßl
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Additional information

Herrn Prof. Dr. U. Schmidt mit herzlichen Grüßen zum 65. Geburtstag gewidmet

Siehe Lit. [2]

Siehe Lit. [3]

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Buchbauer, G., Spreitzer, H., Zechmeister-Machhart, F. et al. Bishomocamphenilon, Bishomocamphen und Bishomocamphenilansäure: Synthesen in der Isocamphanreihe, 32. Mitt.. Monatsh Chem 120, 299–310 (1989). https://doi.org/10.1007/BF00811742

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  • DOI: https://doi.org/10.1007/BF00811742

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