Coupling of ferrocenyl chromium carbene complex with cyclobutenediones

Date

2002-08-15

Author

Zora, Metin
Bekir Peynircioglu, N.

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The coupling of ferrocenyl chromium carbene complex with cyclobutenediones leads to ferrocenyl-substituted 5-alkylidenefuranones and 4-cyclopentene-1,3-diones, methyl ferrocenoate and acetylferrocene in varying amounts. The scope and limitations of these processes are investigated. In comparison with the phenyl analog, ferrocenyl chromium carbene complex has been found to be less reactive. This is also supported by PM3 calculations. The coupling of ferrocenyl chromium carbene complex with cyclobutenediones produces ferrocenyl-substituted 5-alkylidenefuranones and 4-cyclopentene-1,3-diones, methyl ferrocenoate and acetylferrocene in varying amounts. In comparison with the phenyl analog, as supported by PM3 calculations, ferrocenyl chromium carbene complex has been found to be less reactive

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Materials Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/34840

Journal

Journal of Organometallic Chemistry

DOI

https://doi.org/10.1016/s0022-328x(02)01403-1

Collections

Department of Chemistry, Article

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Reaction of Metal-Carbene Complexes with Cyclobutenediones: The First General C-C Bond Insertion Reaction for Fischer Carbene Complexes Zora, Metin (American Chemical Society (ACS), 1993-01-01) Alkylcarbene-chromium complexes react with cyclobutenediones to give 2-alkoxy-4-cyclopentene-1,3-diones in moderate yield, accompanied by varying amounts of 4-cyclopentene-1,3-dione derivatives which result from reduction of the initial product by the chromium byproduct. The reaction is general for a variety of cyclobutenedione derivatives with alkoxy, alkyl, or aryl substituents. The major products of the reaction between arylcarbene complexes and cyclobutenediones are 5-alkylidenefuranone derivatives. A m...
Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene with hydrazines Zora, Metin (Elsevier BV, 2007-10-15) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between (2-formyl-1-chlorovinyl)ferrocene and hydrazine derivatives is described. Depending upon the substitution pattern of hydrazine, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/ aryl-3-ferrocenylpyrazoles. The reaction appears to be general for a variety of hydrazine derivatives.
Synthesis of ferrocenyl pyrazoles by the reaction of 3-ferrocenylpropynal with hydrazinium salts Zora, Metin; Odabasoglu, Mustafa; Bueyuekguengoer, Orhan; Turgut, Guenseli (Elsevier BV, 2008-01-01) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between 3-ferrocenylpropynal and hydrazinium salts is described. Depending upon the substitution pattern of hydrazine derivative, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/aryl-3-ferrocenylpyrazoles. Structures of 5-ferrocenyl-1-phenyl-1H-pyrazole, 1-benzyl-5-ferrocenyl-1H-pyrazole and 2-(3-ferrocenylpyrazol-1-yl)ethanol were identified by X-ray crystallography.
Synthesis of ferrocenyl quinolines Zora, Metin (Elsevier BV, 2008-06-01) A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines.
Addition of 1,3-dicarbonyl compounds to the cycloheptatriene derivatives Südemen, M. Burak; Balcı, Metin; Department of Chemistry (2009) The one electron oxidant Mn(OAc)3 has been used for years for the oxidative addition of 1,3-dicarbonyls to alkenes to give dihydrofuranes. Since cycloheptatriene is in equilibrium with its valance isomer norcaradiene, it will be interesting to study the reaction of CHT derivatives with Mn(OAc)3 in the presence of 1,3-dicarbonyls. In our research, we have observed that unsubstituted cycloheptatriene gave CHT based products. However, when electron withdrawing -CN group was attached to C-7 position of CHT we o...

Citation Formats

M. Zora and N. Bekir Peynircioglu, “Coupling of ferrocenyl chromium carbene complex with cyclobutenediones,” Journal of Organometallic Chemistry, pp. 11–17, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34840.