Oxidation reactions of (2,2'-diphenyl)ethylidene-bridged porphyrin dimers were examined for the synthesis of (2,2'-diphenyl)ethylidene-inserted porphyrin arch tape dimers. These reactions provided, in addition to the target arch tape dimers, unexpected products such as a bicyclo[3.3.0]octane-fused porphyrin dimer, a (2,2'-fluorenyl)ethylidene-inserted porphyrin arch tape dimer, and a