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Competitive formation of cellulose p toluenesulfonate and chlorodeoxycellulose during homogeneous reaction of p toluenesulfonyl chloride with cellulose in n n dimethylacetamide lithium chloride



Competitive formation of cellulose p toluenesulfonate and chlorodeoxycellulose during homogeneous reaction of p toluenesulfonyl chloride with cellulose in n n dimethylacetamide lithium chloride



Carbohydrate Research 208: 183-192



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 (tosylchloride). 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.

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Accession: 007145572

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DOI: 10.1016/0008-6215(90)80098-n


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