The Uncatalyzed addition of acetic acid to norbornadiene

Abstract

The uncatalyzed addition of acetic acid to norbornadiene (I) to give mixtures of ezo-dehydronorbornyl acetate (II) and nortricyclyl acetate (III) was studied. Rates of addition and ratios of II/III (degree of homoallylic rearrangement) were found to be quite sensitive to solvent changes. Addition of acetic acid-O-dl permitted a study of the stereochemistry of addition and a measure of the accompanying Wagner-Meerwein rearrangement. An examimtion of the relationship between homoallylic and Wagner-Meerwein rearrangements has been made.