TBAF and cellulose esters: unexpected deacylation with unexpected regioselectivity.
Tetrabutylammonium fluoride has been found to catalyze the deacylation of cellulose esters. More surprisingly, the deacylation is highly regioselective. Even more remarkably, in contrast with the C-6 regioselectivity of other reactions of cellulose and its derivatives, this deacylation shows substantial selectivity for the removal of the acyl groups from the esters of the secondary alcohols at C-2 and C-3, affording cellulose-6-O-esters with high regioselectivity by a simple one-step process employing no protective groups.
Department of Wood Science and Forest Products, and Macromolecules and Interfaces Institute,  Virginia Tech , 230 Cheatham Hall, Blacksburg, Virginia 24061, United States.
Daiqiang
D
Xu
Kevin J
KJ
Edgar
D000215:Acylation; D000438:Alcohols / Q000737:chemistry; D001709:Biotechnology / Q000379:methods*; D002384:Catalysis; D002482:Cellulose / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D000438:Alcohols; D004952:Esters; D000644:Quaternary Ammonium Compounds; D002482:Cellulose; C009405:tetrabutylammonium; D004121:Dimethyl Sulfoxide