A new synthetic approach for the preparation of polymer supports based on beaded copolymers of styrene and 2,4,5-trichlorophenyl acrylate: Synthesis and swelling behaviour of poly(styrene-co-acrylamide) resins

A new synthetic approach for the preparation of polymer supports/polymeric reagents is reported. The method is based on the chemistry of activated esters, and it is generally simpler than the methods conventionally employed for the preparation of funcationalized resins. Thus, the details of a series of beaded, and predominantly alternate, poly(styrene-co-2,4,5-trichlorophenyl acrylate)s is given. These activated resins were readily converted into highly functionalized poly(styrene-co-acrylamide) resins by aminolysis with a functional groups carrying amine. Resins with low degrees of functionality were obtained by partial aminolysis of the activated resins with a simples amine, and subsequent reaction with a functional group carrying nucleophile, or vice versa. A number of the new resins were examined for their swelling behaviour in a wide range of solvents and were found to show a considerably more general solvent compatibility than either styrene- or N,N-dimethylacrylamide-based resins. The relatively general solvent compatibility of the new resins is briefly discussed in terms of their copolymer structure and its is suggested that the dual “hydrophobic-hydrophilic”, character of these resins may be of important practical implications in, among others, solid phase peptide synthesis.