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Reaction of Metal-Carbene Complexes with Cyclobutenediones: The First General C-C Bond Insertion Reaction for Fischer Carbene Complexes
Date
1993-01-01
Author
Zora, Metin
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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.
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
URI
https://hdl.handle.net/11511/49211
Journal
Organometallics
DOI
https://doi.org/10.1021/om00026a002
Collections
Department of Chemistry, Article
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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...
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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.