The Thermolysis of Bornyl and Iso-Bornyl Acetates

Abstract

Recent investigations in the area of acetate gas phase thermolysis indicate a mechanism which involves a similar transition state despite the acetate used. The reaction preferentially goes through a cis-elimination with the β-hydrogen atoms, proceeding through a six-membered ring transition state. The purpose of this study is to examine the effect of a strained bicyclic ring system upon the mechanism of acetate thermolysis. Throuqh kinetic studies and product identification of the pyrolyzed products of bornyl and iso-bornyl acetate, an insight into the preferred mechanism can be obtained. A previous study (cited later) indicated that the accepted six-membered cis-elimination is not the mechanism which strained bicyclic acetates preferred. This paper will, therefore, examine this question and determine if inconsistent products and kinetics are indeed obtained

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