Advances in the Chemistry of Ambident Enolate and Phenoxide Ions

The reactivities of ambident enolate and phenoxide ions in alkylation reactions are examined. It is shown that the mode of C- and O-alkylation of an ambident anion is determined by the structures of the alkyl group and the group eliminated from the alkylating agent, the nature of the solvent, and the type of counter ion. The influence of each of these factors on the dual reactivity of the enolates of carbonyl and β-dicarbonyl compounds and esters as well as phenoxides and naphthoxides is analysed in detail. The bibliography includes 160 references.

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