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• W2136391362 abstract "The reaction of iso-propoxy stabilized Fischer carbene complexes with ketene acetals gives moderate to excellent yields of cyclopropanone acetals when carried out under a carbon monoxide atmosphere. This is in contrast to the known reaction of methoxy substituted complexes which give cyclic ortho esters under the same conditions. A mechanism is proposed which involves a branch point between the two products as the zwitterionic intermediate resulting from nucleophilic addition of the ketene acetal to the carbene carbon. A 1,3-migration of the methoxyl group to the cationic center leads to the ortho ester and a ring closure by backside attack leads to the cyclopropanone acetal. A double-labeling experiment shows that the 1,3-migration occurs by an intramolecular process that is proposed to involve a bridging oxonium ion. The effect of the isopropoxy group is thus interpreted to be to sterically hinder the formation of a bridged oxonium ion." @default.
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• W2136391362 date "2005-12-01" @default.
• W2136391362 modified "2023-10-03" @default.
• W2136391362 title "The first synthesis of cyclopropanone acetals from the reaction of Fischer carbene complexes with ketene acetals" @default.
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• W2136391362 doi "https://doi.org/10.1016/j.jorganchem.2005.08.025" @default.
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