Quantitative amine functionalization of polymeric organolithium compounds with 3-dimethylaminopropyl chloride in the presence of lithium chloride



The addition of lithium chloride promoted the coupling reaction of hydrocarbon solutions of poly(styryl)lithium (PSLi) and poly(isoprenyl)lithium (PILi) with 3-dimethylaminopropyl chloride to form the corresponding ω-dimethylamino-functionalized polymers. Quantitative amine functionalization was achieved for PSLi and PILi in the presence of 1 and 10 equivalents, respectively, of LiCl in benzene; the functionalization efficiency was only 67% for PSLi and 85% for PILi in the absence of LiCl. The polymer products were characterized by size exclusion chromatography, thin-layer chromatography, and amine end-group titration. The pure amine-functionalized polymers were isolated by silica gel column chromatography. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 145–151, 2000