Protection and Polymerization of Functional Monomers. 30. Anionic Living Polymerization of 4-Alkylstyrenes Containing Acetal-Protected Monosaccharide Residues

Three new para-substituted styrene derivatives, p -[3-(1,2:5,6-di- O -isopropylidene-α- d -glucofuranose-3-oxy)propyl]styrene ( 1 ), p -[3-(1,2:3,4-di- O -isopropylidene-α- d -galactopyranose-6-oxy)propyl]styrene ( 2 ), and p -[11-(1,2:5,6-di- O -isopropylidene-α- d -glucofuranose-3-oxy)undecyl]styrene ( 3 ) were synthesized by phase transfer catalyzed etherifications. Their anionic polymerizations proceed in a living manner in THF at −78 °C using sec -BuLi as the initiator to quantitatively afford polymers with well-controlled molecular weights (6.7−42K) and narrow molecular weight distributions ( M w / M n < 1.06). Novel AB and BA diblock copolymers of 1 and styrene were also successfully synthesized. The stabilities of the living polymer of 1 and the already reported living polymer of m -(1,2:5,6-di- O -isopropylidene-α- d -glucofuranose-3-oxymethyl)styrene ( 4 ) were examined under the polymerization conditions at −78 °C for 22 h and −30 °C for 0.5 h.