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

Abstract

Abstract 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 ( M n ) of 16,000. However, the M n 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