Synthesen in der Isocamphanreihe, 38. Mitt.: Ozonolyse von 2-Acetyl-3,3-dimethylnorborn-5-en und Synthese eines neuen,tricyclischen Ketals mit patchouliartigem Geruch |
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| Authors: | G. Buchbauer H. Spreitzer A. Gruber C. Lux A. Wolfsberger H. Kalchauser |
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| Affiliation: | (1) Institut für Pharmazeutische Chemie, Universität Wien, A-1090 Wien, Österreich;(2) Institut für Organische Chemie, Universität Wien, A-1090 Wien, Österreich |
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| Abstract: | Summary The ozonolysis ofendo-2-acetyl-3,3-dimethylbicyclo[2.2.1]hept-5-ene (endo-1) and itsexo-epimer (exo-1) is described. The reaction products, after reductive work up as well as after oxidative work up, are characterized. The first procedure furnished the corresponding cyclopentane derivatives in good yield, namely 1,1-dimethyl-2-(1-hydroxyethyl)-3,5-bis-hydroxymethyl cyclopentane (2) as a cristalline compound fromendo-1, the epimeric10 as an oil fromexo-1. The oxidative work up furnished in both cases via keto-enol-tautomerism the same acid, 4-acetyl-5,5-dimethyl-1,3-cyclopentane dicarboxylic acid, characterized as its methyl ester. Selective oxidation of the secondary hydroxyl group in2 lead to the novel, tricyclic, even acid stable ketal17, with very interesting olfactory properties.Herrn Prof. Dr. Ulrich Schmidt mit den besten Wünschen zum 70. Geburtstag gewidmet |
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| Keywords: | Acetyl-dimethylbicyclo[2.2.1]hept-5-ene Cu(NO3)2-SiO2 reagent Cyclopentane-1,3-dicarboxylic acid Dimethylcyclopentane derivatives Isocamphane derivatives Ketal Norborn-5-ene derivatives Ozonolysis Patchouli-like odour Trimethyl-dioxa-tricyclo[4.2.2.0]decane |
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