Alkylation of enolate anions formation of enol ethers

G.J. Heiszwolf, H. Kloosterziel

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Abstract

The alkylation of ambident enolate anions-obtained from aliphatic ketones (and one particular type of aldehyde)-was 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., Me2SO) yields mainly enol ethers, the products of alkylation at O. The predominance of alkylation at O over alkylation at C in these fast reactions and the behavior of the various enolate anions are interpreted with the aid of the principle of least motion. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)1153-1169
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume89
Issue number11
DOIs
Publication statusPublished - 1970

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