REDUCTIVE ALLYLATION OF POLY(CHLOROTRIFLUOROETHYLENE)

Treatment of poly(chlorotrifluoroenylene) with allyltin. reagents resu lts in the clean replacement of chlorine by the allyl group under free -radical-chain conditions (AIBN, allyltribtrtyltin), affording about a 10% degree of functionalization. An improved method using one-electro n reduction of the polymer with cobalt(II) (generated by reduction of chloro(pyridine)bis(dimethylglyoximato)cobalt(III) with Mg) and allylt ributyltin gives 50% functionalization Further modification of the all yl group is realized through hydroboration-oxidation to the alcohol an d subsequent Cr(VI) oxidation to the acid. A mechanistic discussion is provided. (C) 1996 John Wiley & Sons, Inc.