Ketone ω-functionalization of polymers prepared by nitroxide-mediated polymerization via addition to a benzyl enol ether

A new method for post-polymerization ω-end-group functionalization of polymers prepared by nitroxide-mediated free radical polymerization (NMP) is presented. Following polymerization, thermolysis in the presence of the enol ether α-benzyloxystyrene results in termination of the polymer with introduction of a phenyl ketone. The ketone group offers the opportunity for further elaboration by hydrazone or oxime formation under mild, physiologically compatible conditions.