Competitive Formation of Cellulose Para-Toluenesulfonate and Chlorodeoxycellulose During Homogeneous Reaction of Para-Toluenesulfonyl Chloride with Cellulose in N,N-Dimethylacetamide-Lithium-Chloride
Document Type
Article
Publication Date
12-15-1990
Department
Polymers and High Performance Materials
Abstract
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.
Publication Title
Carbohydrate Research
Volume
208
First Page
183
Last Page
191
Recommended Citation
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