ASYMMETRIC ANIONIC-POLYMERIZATION OF ALKYL-SUBSTITUTED N,N-DIPHENYLACRYLAMIDE DERIVATIVES

Five novel N,N-diphenylacrylamide derivatives bearing alkyl groups on a phenyl group were synthesized and polymerized with a chiral anionic initiator, the complex of (-)-sparteine and fluorenyllithium, in tolue ne at low temperature. Both position and size of the alkyl-substituent s greatly affected the tacticity and optical activity of the polymer o btained. N,N-Di-4-tolylacrylamide gave a polymer possessing the highes t isotacticity (m = 72%) and specific rotation ([alpha](365)(25) = -42 3 degrees) which may be attributed to the chiral conformation of the m ain-chain. The asymmetric anionic polymerization of N-phenyl-N-(4-toly l)acrylamide gave a chloroform-soluble polymer which was found to cont ain a polymer of high specific rotation([alpha](365)(25) = -1122 degre es) and isotacticity (m = 94%) through fractionation by GPC.