Thermally stable Diels–Alder polymer using an azodicarbonyl compound as the dienophile

Abstract A novel Diels–Alder polymerization system was developed, using an azodicarbonyl compound as the dienophile. A bis(azodicarbonyl) monomer was prepared by quantitative oxidation of bis(diacylhydrazine) with t BuOCl in the presence of pyridine. Diels–Alder polymerization was carried out with a bisdiene monomer, using AgOTf as the catalyst. High thermal stability of the polymer is characteristic for the products of this Diels–Alder polymerization system, in which the Diels–Alder reaction is irreversible. The C=C bond in the Diels–Alder polymer can be cleaved by ozonolysis to give a polyketone.