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Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate |
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| Authors: | Masayuki Kirihara Hiroko Kakuda Yuta Ochiai Asuka Mokuya Akihiko Hatano |
| Affiliation: | a Department of Materials Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan b Laboratory of Chemistry, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama 930-0194, Japan c Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama 930-0194, Japan d Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima-shi, Tokyo 196-8666, Japan |
| Abstract: | Tertiary cyclopropanol compounds react with a catalytic amount of vanadyl acetylacetonate in the presence of oxygen affording β-hydroxyketones and β-diketones. For 3-substituted-bicyclo[4.1.0]alkanols, peroxides are obtained, as are the β-hydroxyketones. Conversely, 2-ethoxycarbonylcyclopropyl silyl ethers produce ethyl γ-oxocarboxylate derivatives given the same reaction conditions. |
| Keywords: | Fragmentation reactions Cyclopropanes Peroxides Vanadium compounds |
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