Reaction of Metal-Carbene Complexes with Cyclobutenediones: The First General C-C Bond Insertion Reaction for Fischer Carbene Complexes

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 mechanism involving oxidative addition of the acyl-acyl C-C bond, followed by carbene insertion and reductive elimination, is proposed.
Organometallics

Suggestions

Coupling of ferrocenyl chromium carbene complex with cyclobutenediones
Zora, Metin; Bekir Peynircioglu, N. (Elsevier BV, 2002-08-15)
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...
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 and structural characterization of a novel seven-coordinate cobalt(II) complex: 2,9-Bis(ethanolamine)-1,10-phenanthrolinechlorocobalt(II) chloride
BAYSAL, AKIN; AYDEMİR, MURAT; DURAP, FEYYAZ; Özkar, Saim; Yildirim, Leyla Tatar (Elsevier BV, 2011-05-31)
Condensation reaction of 2,9-dicarboxaldehyde-1,10-phenanthroline with 2-aminoethanol followed by NaBH4 reduction yielded the polydentate Schiff base ligand 2,9-bis(ethanolamine)-1,10-phenanthroline in its reduced form. This ligand was characterized by elemental analysis, LC-MS, IR, UV-Vis and NMR spectroscopy. Reaction of the reduced Schiff base ligand with aqueous solution of cobalt(II) chloride affords 2,9-bis(ethanolamine)-1,10-phenanthrolinechlorocobalt(II) chloride in high yield. Single crystals of th...
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 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives
Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
Citation Formats
M. Zora, “Reaction of Metal-Carbene Complexes with Cyclobutenediones: The First General C-C Bond Insertion Reaction for Fischer Carbene Complexes,” Organometallics, pp. 248–249, 1993, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/49211.