Synthesis of new monomers by addition reactions of diethylamine to 1,4‐divinylbenzene catalyzed by lithium diethylamide

Addition reactions of diethylamine onto 1,4‐divinylbenzene (DVB) catalyzed by lithium diethylamide were examined to find a synthetic route to a group of new monomers possessing dialkylamino substituents, which is expected to be a starting material for biomedical polymers such as ionic polymer complexes, polycations, and others. It was found that 1‐(2‐diethylaminoethyl)‐4‐vinylbenzene (1) and 1,4‐bis(2‐diethylaminoethyl)‐benzene (2) can be prepared selectively, because the rate of the first step of the addition reaction was twenty times as large as that of the second step. Results of kinetic studies on the addition reactions towards DVB are discussed with the aid of 13C NMR data and compared with other p‐vinylbenzene derivatives.