Anionic ring-opening polymerization of a five-membered cyclic carbonate having a glucopyranoside structure



Anionic ring-opening polymerizations of methyl 4,6-O-benzylidene-2,3-O-carbonyl-α-D-glucopyranoside (MBCG) were investigated using various anionic polymerization initiators. Polymerizations of the cyclic carbonate readily proceeded by using highly active initiators such as n-butyllithium, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene, whereas it did not proceed by using N,N-dimethyl-4-aminopyridine and pyridine as initiators. In a polymerization of MBCG (1.0 M), 99% of MBCG was converted within 30 s to give the corresponding polymer with number-averaged molecular weight (Mn) of 16,000. However, the Mn of the polymer decreased to 7500 when the polymerization time was prolonged to 24 h. It is because a backbiting reaction might occur under the polymerization conditions. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013