Model compounds of cellulose: Trityl ethers substituted exclusively at C-6 primary hydroxyls

Abstract

Triphenylmethylcellulose (trityl cellulose) in which substitution of only the primary hydroxyls at C-6 on the cellulose chain occurs has been prepared using superdry cellulose derived from gel cellophane. The diacetate and dicarbanilate derivatives substituted exclusively at C-2 and C-3 secondary hydroxyls could then be prepared. Detritylation afforded the cellulose dicarbanilate or diacetate. Proof that no secondary substitution occurred was afforded by elemental analysis and by tosylation followed by replacement of the tosyl group with iodine. Because of the low D.P. of the cellulose and the ease with which the cellulose polymers can be cast into films, these cellulose model compounds might find utility for studying the effect of reactions at either the primary or the secondary hydroxyls of cellulose.