A new strategy for the synthesis of end-functionalized polyisobutylene (PIB) oligomers is detailed. Commercially available vinyl-terminated PIB oligomers were modified to form aniline-terminated PIB via an aromatic electrophilic substitution reaction. The PIB-bound aryl amines so formed were then converted into diazonium salts using isopentyl nitrite and an acid in methylene chloride. These salts served as versatile intermediates in synthetic reactions affording azo dye-containing PIB derivatives and other terminally-functionalized PIB derivatives not readily available by other reactions. The advantages and limitations of various name reactions including diazo couplings, Sandmeyer reactions, dediazoniations, and Heck reactions are discussed. The kinetics of polar substitution reactions at the termini of these nonpolar oligomers and the effects of solvent on these reactions were also examined. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49:1772-1783, 2011