Abstract

The reaction of lithium pinacolonate with seven para-substituted benzaldehydes has been examined in tetrahydrofuran and acetonitrile. Reactions were clean, complete, and instantaneous at 25 o C, and heats of reaction were determined by titration calorimetry. Fairly good (R=0.96) correlations between heats of reaction and the usual Hammett σp substituent parameters were obtained although the ionization of substituted benzoic acids is scarcely an appropriate model for the aldol reaction in nonpolar media

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