2,5-Bis(chloromethyl)-1,3,4-oxadiazole was synthesized and dehydrohalogenation of this model compound was investigated under various base conditions. The formation of an intermediate with quinodimethane-type structure is suggested for reaction in EtONa/EtOH. Polymerization of this intermediate proceeds via an anionic mechanism to form poly(1,3,4-oxadinazole-2,5-diyl-1,2-vinylene). Polymerization at a toluene/water interface results in shorter polymerization times, milder conditions, higher molecular weights, higher yields and fewer defects in the polymer as compared to the corresponding polycondensation route.