Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones

Date

2007-05-07

Author

Zora, Metin
Bueyuekguengoer, Orhan

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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 alpha, beta-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 oc 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 cyclopentadienome intermediates.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/35972

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2007.03.001

Collections

Department of Chemistry, Article

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Citation Formats

M. Zora and O. Bueyuekguengoer, “Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones,” TETRAHEDRON, pp. 4018–4026, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35972.