One-pot exchange reaction of acyl hydrazone combined with radical polymerization of styrene derivatives bearing acyl hydrazone moieties

We developed a one-pot reaction combining an exchange reaction of the benzylidene moiety in an acyl hydrazone with styrene radical polymerization. The one-pot reaction of a styrene derivative bearing a 4-(dimethylamino)benzylidene acyl hydrazone moiety was conducted in the presence of 4-cyanobenzaldehyde and pyridinium p-toluene sulfonate/H2O for the exchange reaction and AIBN as the radical polymerization initiator in N,N-dimethylformamide at 70 degrees C for 20 h. The exchange reaction proceeded quantitatively, with the 4-(dimethylamino)benzylidene acyl hydrazone moiety being exchanged with 4-(methoxy)benzylidene acyl hydrazone, and polymerization proceeded smoothly to provide the corresponding polymer in 70% yield. Compared to traditional stepwise methods and polymer post-polymerization modifications, this one-pot system exhibits distinct advantages for the facile and efficient preparation of various functional polymers. (c) 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019