Living polystyryl lithium was synthesized by anionic polymerization under the protection of argon at normal pressure, and styrene, toluene, tetrahydrofuran, and n-butyllithium were used as a monomer, solvent, polar reagent, and initiator, respectively. Then, polystyrene oligomers containing several pendent epoxy groups with well-defined structures and narrow molecular weight distributions (weight-average molecular weight/number-average molecular weight < 1.1) were prepared by the reaction of polystyryl lithium with glycidyl methacrylate. The prepared oligomers were characterized with gel permeation chromatography, Fourier transform infrared spectroscopy, H-1-NMR, and the hydrochloric acid/dioxane argentimetric method. The effects of the glycidyl methacrylate dosage, molar mass of polystyrene precursors, copolymerization time, and temperature on the content of side epoxy groups were also investigated. The results confirm that 1,1-diphenylethylene-end-capped polystyryl carbanion could initiate glycidyl methacrylate in toluene in the presence of lithium chloride and a small amount of tetrahydrofuran, and the content of the side epoxy groups could be adjusted. (C) 2010 Wiley Periodicals, Inc. J Appl Polym Sci 117: 2566-2574,2010