Facile preparation of deoxyiodocellulose and its conversion into 5,6-cellulosene

Treatment of 6-chloro-6-deoxycellulose with sodium iodide in 2,5-hexanedione gave 6-deoxy-6-iodocellulose; >80% of the chlorine atoms were replaced. 6-Deoxy-6-iodo-d-glucose was identified by g.l.c.-m.s. in hydrolyzates of deoxyiodocellulose. Acetylated 6-deoxy-6-iodocellulose was converted almost quantitatively into 5,6-cellulosene acetate, which was characterized by hydrolyzing the product and converting the resultant dicarbonyl sugar into an isopropylidene acetal 10. The changes of molecular-weight distribution during iodination and dehydroiodination were investigated by gel-permeation chromatography.