COMPETITIVE FORMATION OF CELLULOSE PARA-TOLUENESULFONATE AND CHLORODEOXYCELLULOSE DURING HOMOGENEOUS REACTION OF PARA-TOLUENESULFONYL CHLORIDE WITH CELLULOSE IN N,N-DIMETHYLACETAMIDE LITHIUM-CHLORIDE

The homogeneous preparation of a cellulose p-toluenesulfonate (tosylate) in N,N-dimethylacetamide-lithium chloride (DMAc-LiCl) is hampered by solvolysis of the p-toluenesulfonyl chloride (tosyl chloride). This Vilsmeier-Haack type reaction results in competitive formation of cellulose p-toluenesulfonate and chlorodeoxycellulose. Highly p-toluenesulfonylated cellulose may be prepared in DMAc-LiCl with minimal incorporation of chlorine by utilization of either triethylamine or 4-dimethylaminopyridine as base. A mechanism for the competing series of reactions is postulated. © 1990.