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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

✍ Scribed by Charles L. McCormick; Timothy R. Dawsey; J.Kent Newman

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 592 KB
Volume: 208
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)80098-n

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✦ Synopsis

The homogeneous preparation of a cellulose p-toluenesulfonate (tosylate) in N,N-dimethylaceta-mid+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 cellulosep-toluenesulfonate and chlorodeoxycellulose.

Highly p-toluenesulfonylated cellulose may be prepared in DMAc-LiCl with minimal incorporation ofchlorine by utilization of either triethylamine or 4-dimethylaminopyridine as base. A mechanism for the competing series of reactions is postulated.

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