CYCLOPOLYMERIZATION OF "(E,E)-[6.2]PARACYCLOPHANE-1,5-DIENE

Polymerization of (E,E)- left bracket 6. 2 right bracket paracyclophane-1,5-diene proceeds by an intra-intermolecular mechanism to give a polymer containing a left bracket 3. 2 right bracket paracyclophane in the repeat unit. Polymerization occurs with either free radical or cationic initiation; anionic initiation was unsuccessful. Cationic polymerization is favored and appears to proceed through a stabilized carbonium ion intermediate. Spectroscopic and model compound studies are consistent with the proposed polymer structure. Thermal analyses of the polymer indicate a complex thermooxidative behavior in the presence of oxygen, while depolymerization occurs above about 400 degree C in an inert atmosphere.