The Catalyzed addition of acetic acid to norbornadiene

Abstract

An investigation of the acid-catalyzed addition of acetic acid to norbornadiene (I)to form ezo-dehydronorbornyl acetate (II) and nortricyclyl acetate (III) has been carried out. Catalysis by sodium perchlorate was similar that of sulfuric acid and perchloric acid. The addition of acetic acid-0-dl resulted in a larger degree of "scrambling" of deuterium in the acetates when catalyzed than when uncatalyzed. The ratio of esters (II/III) was essentially constant in the product when perchloric acid was the catalyst. When sulfuric acid was the catalyst, the product ratio was variable, and favored the olefinic acetate more than when perchloric acid was the catalyst. Both sulfuric acid and perchloric acid catalyzed reactions exhibited sensitivity to solvent effects as shown by rate and product-ratio variations.