Kinetical experiments on ozonization reactions: V. The ozonization of some norcaradiene derivatives

The addition of ozone to some norcaradiene derivatives has been studied quantitatively. The reaction of ozone with methyl and ethyl norcaradiene‐7‐carboxylate (I) results in the formation of a diozonide. Ethyl benzonorcaradiene carboxylate (II) forms a monozonide, which subsequently reacts at a much lower reaction rate, probably producing a tetraozonide. These results are in opposition to the hypothesis of Badger, stating that the reactivity of the double bond reagents in norcaradiene derivatives towards “double bond reagents” is greatly reduced by conjugation with the cyclopropane ring. Pure methyl norcaradiene‐7‐carboxylate has been prepared via its dibromo‐derivative.