A Study of the Direct and Sensitized Reactions of 1,3-Cyclooctadiene and 1,3,5-Cycloheptatriene in Solution

A number of experiments were carried out in an attempt to determine the course of bicyclic isomerization in cycloheptatriene and 1,3-cyclooctadiene. Results, inconsistent with literature reports but showing definite consistency within the course of the experiments, led to the further examination of both the direct and benzophenone-sensitized reaction of the above compounds. Attempts were made at fractionation by preparative vapor chromatography. The fractions obtained were examined by NMR spectroscopy in the case of 1,3-cyclooctadiene. A crystalline product obtained from the sensitized reaction of cycloheptatriene was also partially characterized.