Ring-opening of tertiary cyclopropanols derived from β-diketones |
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Authors: | Le-Zhen Li |
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Institution: | Department of Chemistry, University of Science and Technology of China, Hefei 230026, PR China |
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Abstract: | The ring-opening reaction of 1,2-disubstituted cyclopropanols, prepared from β-diketones, mediated by Cu(NO3)2, p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave α-methylene-γ-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2Cl2 afforded α-methyl-γ-diketones as the major product with minor amounts of δ-diketones. The 2,3,5-trisubstituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of δ-diketones, particularly for substrates with an aromatic group on the cyclopropane. |
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Keywords: | 1 2-Disubstituted cyclopropanol Cu(NO3)2 α-Methyl-γ-diketone 2 3 5-Trisubstituted furans |
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