Abstract
Three types of N-substituented maleimides having (S)-phenylalaninol esters (RBEMIs) were polymerized with anionic or radical initiators to obtain optically active poly (RBEMI) s. Specific rotations of the poly (RBEMI) s were influenced by N-substituents, initiator, solvent, and temperature. Among RBEMIs, (S)-(-)-N-2-Acetoxy-1-benzyl- ethyl maleimide (AcBEMI) and (S)-(-)-N-2- pivaloyloxy-1-benzylethyl maleimide (PvBEMI) yielded the corresponding polymers with higher levorotations compared with those of the monomer itself and of the model compound. CD, GPC, and 13C NMR measurements of the poly (RBEMI) s revealed that optical activity of the poly (RBEMI) s with high levorotations was attributable not only to the chiral N-substituent, but also to chiral carbons in the threo-diisotactic main chain.
