Simple synthesis of polymeric primary aromatic amines

Summary A new simple and versatile method of obtaining polymers bearing aromatic primary amino groups was developed. The method consists in the reaction of an alkylating polymer with sodium 4-acetylaminobenzenesulfinate and subsequent deacetylation of the intermediate polymer by acid hydrolysis. Alkylating polymers such as chloromethylated polystyrene resin, tosylated macroporous poly (2-hydroxyethyl methacrylate), macroporous poly(glycidyl methacrylate) and PVC were used in the alkylation performed either in an organic swelling solvent or in an aqueous suspension under phase transfer catalysis conditions. Yields in the alkylation step depend largely on the type of the alkylating group, hydrolysis yields are essentially quantitative.