Cyclopolymerization of N,N′-bis(phenylsulfonyl)-N,N′-divinylethylenediamine and the related monomer

Abstract

The cationic polymerization of 1,7-diene monomers 1a and 1b produced polymers 2a and 2b with seven-membered rings as a precursor of azacrown polymer. SnCl4, and BF3·OEt2 in dichloromethane were effective for polymerization. Sulfuric acid was less effective and trifluoroacetic acid was ineffective. The molecular weights reached a maximum of 17000 and 34000 for 2a and 2b, respectively. Monomer 1a polymerized with 100% cyclization. Although all the vinyl groups participated also in the polymerization of 1b. GPC traces of 2b showed a pronounced leading in the region of higher molecular weight by some participation of chain branching. The monomers were unstable to convert to 2-methylimidazolidines 9a and 9b, when allowed to stand in contact with the atmosphere. The polymerization formed seven-membered ring units, but the cyclization reaction resulted in five-membered ring compounds.