Reactivity of ambident anions : Hardness of alkyl groups and symbiotic effect in alkylation of ambident anions
作者： A.L. Kurts , N.K. Genkina , A. Macias , L.P. Beletskaya , O.A. Reutov
DOI: 10.1016/S0040-4020(01)98183-9
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摘要: Abstract Effect of the alkylating agent nature in case O- and C-alkylation both ethyl acetoacetate acetylacetonate anions is reported. The value O/C-ratio depends on three factors: polar effect alkyl substituents agents, steric groups symbiotic leaving groups. relative contributions first two effects group nature. predominates when a soft base (iodide, bromide, chloride) decreases order sec. Bu > iPr Et Me. sequence opposite to given above for hard group, tosylate, this Pearson's hardnesses. influence also A strong was found methylation enolate ions. In ethylation, less detectable; secondary almost non-susceptible group.
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