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The alkylation of ambident enolate anions ‐ obtained from aliphatic ketones (and one particular type of aldehyde) ‐ has been studied using various solvents, bases, alkylating agents and substrates. Alkylation with a reactive alkylating agent (dialkyl sulfates, triethyloxonium fluoroborate) in an aprotic polar solvent (e.g. dimethyl sulfoxide) yields mainly enol ethers, the products of alkylation at oxygen. The predominance of alkylation at oxygen over alkylation at carbon in these fast reactions and the behaviour of the various enolate anions are interpreted with the aid of the principle of least motion.
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Heiszwolf et al. (1970) studied this question.
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