Reactivity of ambident anions. Kinetic alkylation of β-ketoester alkaline enolates by ethyl tosylate in hexamethylphosphortriamideстатья
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Аннотация:The alkylation of K- and Cs-enolates of ethyl γ,γ-dimethyl-, ethyl γ,γ,γ-trimethylacetoacetates and also Cs-enolate of ethyl γ,γ,γ-trifluoroacetoacetate by ethyl tosylate in HMPT is reported. The degree of dissociation of β-ketoester Cs-enolates in the same solvent was measured by the conductometric method. The rates of both O- and C-ethylations of the enolate ion were measured. The pKa of the corresponding β-ketoesters were measured in DMF. The reactivity of the enolates investigated was found to be proportional to their basicity.