Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones |
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Authors: | Metin Zora Tülay Asl? Tumay |
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Institution: | a Department of Chemistry, Faculty of Arts and Sciences, Middle East Technical University, 06531 Ankara, Turkey b Department of Physics, Faculty of Arts and Sciences, Ondokuz May?s University, 55139 Kurupelit Samsun, Turkey |
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Abstract: | The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and α,β-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy group ends up α to the ferrocenyl moiety. In contrast, where no addition of water occurs, the alkenic bond is reduced to give 2-cyclopentenones. A secondary reaction product, namely 4-cyclopentene-1,3-dione, is formed by hydrolysis of the cyclopentadienone intermediates. |
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Keywords: | Fischer metal carbene Chromium-carbene complex Ferrocene Ferrocenyl alkynes Carbocyclic five-membered rings Cyclopentenones Cyclopentenediones Cyclobutenones α β-Unsaturated aldehydes Coupling |
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