Abstract
Isopropylation of the sodium salt of ethyl α-ethyl-acetoacetate, II, has been studied kinetically in two aprotic solvents, DMSO and HMPT. Second order rate constants for C-alkylation, O-alkylation, and propene formation are compared with those of the cyclic β-keto ester systems, I-n. In each reaction mode, the acyclic enolate is significantly more reactive than the cyclic ones. Conductance studies suggest that the greater reactivity of the sodium enolate of II may be attributed to its higher degree of dissociation in the aprotic solvents and the ability of the free ion to assume a “W” shape. The superior ability of HMPT to enhance nucleophilic reactivity, in general, and to promote O-alkylation, in particular, is noted.
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