TAUTOMERISM OF ETHYL 3-OXOBUTYRATE AND IT S 2-ALKYL DERIVATIVES

Effects of substituents, solvents, concentration, and temperature on t automerization of ethyl 3-oxobutyrate and its 2-alkyl derivatives were studied. The tautomeric equilibria of ethyl 3-oxobutyrate depend main ly on the polarity and hydrogen-bond donor acidity of solvents. On the other hand, the tautomerization of the 2-methyl derivative is indepen dent of the solvent. Keto-enol interconversion of the keto esters shif ts from the keto form to the enol form with an increase in temperature . In addition, rate constants for interconversion from the keto to the enol of ethyl 2-butyl-3-oxobutyrate were determined using H-D exchang e reaction.