Synthesis of end-functionalized (1→6)-2,5-anhydro-D-glucitols via anionic cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-methyl-D-mannitol for preparing graft copolymers

Abstract

End-functionalized (1→6)-2,5-anhydro-3,4-di-O-methyl-D-glucitols (3a-c) were synthesized by the anionic cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-methyl-D-mannitol (1), followed by treatment with a terminating agent such as 4-vinylbenzyl (2a), oxetanyl (2b), and methacryloyl group (2c). The end-functionalization proceeded in a high efficiency at 73-98%. The radical copolymerization of styrene with 3a yielded a polymer (5a) whose GPC trace exhibited a unimodal peak. 5a was polystyrene with (1 → 6)-2,5-anhydro-3,4-di-O-methyl-D-glucitol as pendant groups whose structure was confirmed by the 1H NMR spectrum.