Thermochemical studies of carbonyl reactions. 4. Enthalpies of hydrolysis of norbornyl ketals

KB Wiberg, WC Cunningham Jr

Index: Wiberg, Kenneth B.; Cunningham, Wells C. Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 679 - 684

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Citation Number: 8

Abstract

The dimethyl ketals of norbornanone and of eight methyl-substituted norbornanones were prepared, and the enthalpies of hydrolysis were determined. The compounds were chosen to provide a variety of steric interactions between the methyl substituents and the ketal group, much of which would be relieved on going to the ketone. The enthalpies of reaction varied by over 4 kcal/mol. The experimental data were modeled by molecular mechanics ( ...