PREPARATION OF CELLULOSE DERIVATIVES VIA RING-OPENING REACTIONS WITH CYCLIC REAGENTS IN LITHIUM-CHLORIDE N,N-DIMETHYLACETAMIDE

Reactivity of cellulose hydroxyl functional groups to strained-ring systems was examined in the lithium chloride/N, N-dimethylacetamide solvent. Epoxide reagents were unreactive to cellulose hydroxyl groups in nucleophilic ring-opening reactions. Cyclic anhydrides and lactones readily reacted in the presence of triethylamine, while 1,3-propane sultone reacted with the competing chloride anion in the DMAc/LiCl solvent. ϵ-Caprolactone reacted with cellulose to form a hydroxy-terminal ester derivative by an addition–elimination mechanism. A novel cyclic iminium chloride cellulose derivative and subsequent hydrolysis products were prepared. © 1990, American Chemical Society. All rights reserved.