Synthesis of telechelic methyl methacrylate and styrene oligomers with fluorophenyl ketone end groups by the ozonolysis of copolymers containing 4-fluorophenyl butadiene units

Abstract

2,3-Di-(4-fluorophenyl)buta-1,3-diene has been prepared and copolymerized with methyl methacrylate and with styrene (ST) by a radical mechanism. In both cases, cleavage of the residual carbon-carbon double bonds of the diene units in the copolymer with ozone leads to telechelic oligomers with 4-fluorophenyl ketone end groups. 19F n.m.r. spectra of the copolymers and oligomers show that the diene units are incorporated predominantly in 1,4-configurations with little or no 1,2-enchainment. Also, a ST-2-(4-fluorophenyl)buta-1,3-diene copolymer has been prepared and cleaved by ozonolysis to give an oligomer with both 4-fluorophenyl ketone and carboxylic acid end groups. In this system also, the 19F n.m.r. spectra of the copolymer and oligomer show that the diene is incorporated almost exclusively in the 1,4-configuration.