SYNTHESES AND RADICAL POLYMERIZATIONS OF OPTICALLY-ACTIVE (METH)ACRYLAMIDES HAVING AMINO-ACID MOIETIES

Syntheses and radical polymerizations of several (meth)acrylamides hav ing L-amino acid moieties were examined. The monomers were prepared by the reactions of L-amino acid ester hydrochlorides with (meth) acrylo yl chloride in the presence of triethylamine in satisfactory yields. R adical polymerizations of the monomers were carried out in the presenc e of AIBN (1 mol %) in bulk and in several solvents to afford the corr esponding polymers in satisfactory yield. The glass transition tempera tures and specific rotations of the polymers depended on the substitue nts of the L-amino acid moieties. Nearly the same specific rotations w ere observed for the monomers and the model compounds of the polymer u nits, N-pivaloyl amino acid methyl esters. On the contrary, the specif ic rotations of the polymers shifted to the negative direction in ca. 30 degrees. The interaction between the polymer side chains might affe ct the changes in the specific rotations from monomers to polymers. (C ) 1997 John Wiley & Sons, Inc.