Synthesis of aromatic polyethers by Scholl reaction. VII. Oxidative polymerization of 2,2-bis[4-(1-naphthoxy)phenyl]propane and 2,2-bis [4-(1-naphthyl)phenyl]propane

The synthesis and the mechanism of oxidative polymerization of 2,2-bis4-(1-naphthoxy)phenyl]propane ( 4 ) and 2,2-bis4-(1-naphthyl)phenyl]propane ( 9 ) are presented. Both monomers polymerize by two different propagation steps. The first one represents a cation-radical dimerization of the naphthyl groups to dinaphthyl structure. H⁺FeCl₄]^? generated from the first propagation step initiates a transalkylation reaction which provides structural units containing isopropylidenic groups inserted between phenyl and naphthyl, and between two naphthyl groups, respectively. Since the phenyl groups resulted from the second propagation reaction are unreactive in both the oxidative coupling and the transalkylation steps this polymerization reaction leads to polymers with low molecular weights containing phenyl chain ends.