Regioselective chlorination of cellulose esters by methanesulfonyl chloride

Carbohydrate Polymers
Chengzhe GaoKevin J Edgar

Abstract

Regioselective chlorination of cellulose is challenging due to its low reactivity, the small reactivity differences between cellulosic hydroxyl groups, and the high and diverse reactivity of most common chlorinating agents. Halogenation of cellulose affords useful precursors for subsequent nucleophilic substitution reactions, permitting incorporation of new functionality. Herein we report a simple and efficient pathway for preparation of 6-chloro-6-deoxycellulose esters and their derivatives. Cellulose acetate (degree of substitution (DS) 1.75, CA320S) can be chlorinated by essentially quantitative reaction of the primary alcohol groups with methanesulfonyl chloride (MsCl), yielding 6-chloro-6-deoxy cellulose acetate. Characterization methods including 1H NMR, 13C NMR, FT-IR spectroscopy, and elemental analysis, demonstrated chemo- and regioselective C-6 chlorination. We also demonstrate that chlorinated cellulose acetate is a useful intermediate for displacement reactions with nucleophiles including sodium azide, amines, and thiols to prepare functional cellulose ester derivatives.

References

Sep 29, 2001·Advanced Drug Delivery Reviews·M ThanouH E Junginger
Apr 30, 2005·Angewandte Chemie·Dieter KlemmAndreas Bohn
Apr 29, 2011·Biomacromolecules·S Carter FoxKevin J Edgar
Jan 11, 2012·Biomacromolecules·Daiqiang Xu, Kevin J Edgar
Apr 13, 2013·Biomacromolecules·Xueyan ZhengKevin J Edgar
Jun 20, 2012·Carbohydrate Polymers·Martin GerickeThomas Heinze
Mar 31, 2015·Carbohydrate Polymers·Ruoran Zhang, Kevin J Edgar
Aug 8, 2015·Biomacromolecules·Shu Liu, Kevin J Edgar
Nov 18, 2015·Carbohydrate Polymers·Ruoran ZhangKevin J Edgar
Feb 23, 2017·Carbohydrate Polymers·Shu Liu, Kevin J Edgar
Jun 6, 2017·Carbohydrate Polymers·Ruoran ZhangKevin J Edgar

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Citations

Sep 11, 2018·Biomacromolecules·Chengzhe Gao, Kevin J Edgar

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