Abstract: The preparative electrooxidation of 2-phenylnorbornene (1) leads to the formation of a dienic oxidative coupling product 2. Analysis of the anodic behavior of 1 by cyclic voltammetry indicates a novel curve crossing, the first such experimental observation in an electrooxidation. An ECE mechanism with significant redox cross reaction is suggested as an explanation for this unusual observation.
![3-phenylbicyclo[2.2.1]hept-2-ene Structure](https://image.chemsrc.com/caspic/223/4237-08-5.png)
![N-(3-phenyltricyclo[2.2.1.02,6]heptan-3-yl)acetamide Structure](https://image.chemsrc.com/caspic/047/85267-41-0.png)
![3,3'-diphenyl-2,2'-bi(bicyclo[2.2.1]heptane-2,2'-diene) Structure](https://image.chemsrc.com/caspic/450/85267-39-6.png)