Vinyl polymers with aromatic substituents, 2. Polymerization of 9-allylanthracene and structures of the polymers

Radical, cationic, and Ziegler-Natta polymerizations of 9-allylanthracene ( 1 ) were carried out. The radical polymerization was found to be an inefficient method leading to oligomers with complex structure. Reaction of initiator radicals and growing macroradicals with the anthryl group or with the allylic hydrogen leads to resonance stabilized radicals which stop the polymerization. The cationic and Ziegler-Natta polymerizations gave a copolymer with 9-anthrylmethylethylene units ( 8 ) (from normal 1,2 addition) and 9,10-anthrylenepropylene units ( 11 ) (from the electrophilic attack of carbocations at the aromatic nucleus). Low polymerization temperatures lead to a preference for the alkylation reaction.