New optically active heterocyclic polyimides with (-)-camphor sulfonic acid ester moieties

(-)-Camphor-10-sulfonyl chloride [(1R)-camphor-10-sulfonic acid chloride] 1 was reacted with isoeugenol 2 in chloroform, and a new optically active is oeugenol ester derivative 3 as a chiral monomer was obtained with a high yi eld. Thus, 4-phenyl-1,2,4-triazoline-3,5-dione (PhTD)4 was allowed to react with compound 3. The reaction was very fast and gave only one diastereomer of 5 via the Diels-Alder and ene pathways with an excellent yield. The pol ymerization reactions with bistriazolinediones[bis(p-3,5-dioxo-1,2,4-triazo iin-4-ylphenyl)methane 6 and 1,6-bis(3,5-dioxo-1,2,4-triazolin-4-yl)hexane 7] were carried out in N,N-dimethyl-acetamide (DMAc) at room temperature. T he reactions were exothermic and fast and gave new optically active polymer s 8 and 9 via the repetitive Diels-Alder-ene polyaddition reactions. The re sulting polymers were optically active and thermally stable. Some structura l characterization and physical properties of these new heterocyclic polyim ides are reported.