Title

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