POLYMERS AS REAGENTS AND CATALYSTS. 39. INTRODUCTION OF PHENYLAMIDO AND PHENYLHYDRAZIDO GROUPS INTO A CROSSLINKED STYRENE-ACRYLATE MATRIX

Marko Zupan, Peter Krajnc, and Stojan Stavber

Laboratory for Organic and Bioorganic Chemistry, Faculty of Chemistry and Chemical Technology and "J. Stefan" Institute, University of Ljubljana, Aškerèeva 5, Ljubljana, Slovenia

Abstract

Crosslinked copoly(styrene-p-nitrophenylacrylate) (1) was hydrolyzed to copoly(styrene-acrylic acid) (2) while further transformation with thionyl chloride gave copoly(styrene-acryloyl chloride) (3). Room temperature reaction of copoly(styrene-acryloyl chloride) (3) in acetonitrile with aromatic amines (aniline, pentafluoroaniline) and aromatic hydrazines (phenylhydrazine, pentafluorophenylhydrazine) gave the corresponding amides (4, 5) and hydrazides (6, 7). The swelling abilities of these amides and hydrazides depended on the type of functional group (amido, hydrazido), aromatic moiety (phenyl ring, pentafluorophenyl ring) and solvent polarity (chloroform, dimethylformamide, perfluorodecaline, perfluorooctane, perfluorocyclic ethers C₈F₁₆O). No significant enhancement in swelling capacity in perfluoro carbonated solvents was achieved by substitution of the phenyl ring by fluorosubstituted rings.