Competitive Formation of Cellulose Para-Toluenesulfonate and Chlorodeoxycellulose During Homogeneous Reaction of Para-Toluenesulfonyl Chloride with Cellulose in N,N-Dimethylacetamide-Lithium-Chloride
Polymers and High Performance Materials
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.
McCormick, C. L.,
Dawsey, T. R.,
Newman, J. K.
(1990). Competitive Formation of Cellulose Para-Toluenesulfonate and Chlorodeoxycellulose During Homogeneous Reaction of Para-Toluenesulfonyl Chloride with Cellulose in N,N-Dimethylacetamide-Lithium-Chloride. Carbohydrate Research, 208, 183-191.
Available at: https://aquila.usm.edu/fac_pubs/7508