Protection and Polymerization of Functional Monomers. 28. Anionic Living Polymerization of Styrene Derivatives Containing Acetal-Protected Monosaccharide Residues

Six styrene derivatives meta-substituted with acetal-protected glucofuranoses ( 1 ) and ( 2 ), galactopyranose ( 3 ), fructopyranose ( 4 ), and sorbofuranose ( 5 ) and para-substituted with acetal-protected glucofuranose ( 6 ) were synthesized by the Williamson reactions of m - or p -(chloromethyl)styrene with the corresponding protected monosaccharides in DMF and were anionically polymerized. The anionic polymerizations were carried out with s -BuLi in THF at −78 °C for 30 min. Among the monomers, 1 − 5, were found to undergo anionic living polymerization to afford quantitatively the polymers of predictable molecular weights and narrow molecular weight distributions ( M w / M n < 1.13). Novel well-defined block copolymers, polystyrene- block -poly( 1 ) starting either from living polystyrene or the living polymer of 1, were successfully synthesized. By contrast, no appreciable polymerization of 6 occurred under identical conditions.