Ring‐opening polymerization of a sugar episulfide

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Abstract
Ring‐opening polymerization of 5,6‐dideoxy‐5,6‐epithio‐1,2‐O‐isopropylidene‐α‐L‐idofuranose is catalyzed by boron trifluoride at 60°C. Soluble polymer is produced at monomer: catalyst ratio of 7 : 1 and monomer concentration 0.077M after 1 1‐hr. polymerization period. This polymer has a wide molecular weight distribution. A number‐average molecular weight of 72,000 is found for the first 40% of the polymer precipitated from a N,N‐dimethylformamide solution by the addition of water. Polymer is produced in increasing amounts as temperature is raised, catalyst concentration increased, and as water concentration is decreased. Transglycosylation may be the cause of branch formation or crosslinking. Hydrolysis of the soluble polymer removes isopropylidene groups to produce a water soluble reducing polymer which oxidizes with hypoiodite to a polymer containing carboxyl groups.

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