The radical cation (3·+) of 9-methylenebicyclo[4.2.1]nona-2,4,7-triene undergoes rapid intramolecular cyclization to generate an isomeric radical cation (15·+) derived from a tetracyclic structure. In contrast, the hydrocarbon 15 suffers retrocyclization to regenerate 3. The comparative stability of 15·+ is ascribed to its bishomoaromatic character. Four radical cations of less unsaturated model compounds support the assigned structure.
All Science Journal Classification (ASJC) codes
- Colloid and Surface Chemistry