Aromatic Polynitro Ether Derivatives of Cellulose

The nucleophilic reaction of sodium cellulosate in the form of membrane or cotton fabric with 2,4-dinitrohalo-benzenes, 2,4,6-trinitrochlorobenzene, 2,4,6-trinitrobenzyl bromide, and 2,4,6-trinitrostyrene was investigated. The degree of substitution attained with the dinitroaryl derivatives was much higher than that with the trinitroaryl derivatives. The reaction proceeded through Meisen-heimer complexes, which in the case of the trinitro derivatives could be isolated. The ability of the polynitro phenyl ether derivatives of the cellulose to form n- and n-complexes was investigated using naphthalene and p-toluidine. No -n- complex was formed with the former, and the latter gave complexes only with the 2,4,6-trinitrobenzyl or -phenethyl cellulose derivatives but not with the trinitrophenyl. The results were explained as due to steric hindrance from the polymeric cellulosic backbone.