Synthesis of functionalized linear poly(divinylbenzene). III. Synthesis of polymeric delocalized carbanion of poly(divinylbenzene) and its reactions

Abstract

AbstractA polymeric delocalized carbanion of poly(divinylbenzene) [poly(DVB)] (2) was obtained by the proton abstraction with alkyllithium from the acidic methine moieties (HA) of linear poly(DVB) (1), which was prepared by the polymerization of DVB initiated by acetyl perchlorate. The formation of polyanion 2 was confirmed by UV–visible spectroscopy (λmax = 630 nm) and the reaction with methyl iodide to give methylated poly(DVB). Delocalized polyanion 2 reacted with various electrophilic reagents in THF at 60°C, to yield poly(DVB) derivatives having pendant trimethylsilyl, vinyl, vinyloxyl, hydroxyl, and carboxyl groups. Proton abstraction with base and subsequent reactions with electrophiles were also studied with the linear unsaturated dimer of styrene (1,3‐diphenyl‐1‐butene), as a model for poly(DVB) 1.