The syntheses of new polyisobutylene macromonomers with methacrylate, acrylate, vinyl ether, and glycidyl ether end-functionality have been accomplished using simple nucleophilic substitution reactions of bromoallyl end-functional polyisobutylene. Use of a phase transfer catalyst tetrabutylammonium bromide significantly increased the rate of substitution reactions. The macromonomers were characterized by H-1, COSY, and C-13 NMR spectroscopic, GPC, and MALDI-TOF MS analyses. The end-functionality was calculated to be similar to 2 in all the cases. The GPC-RI traces were identical to the precursor bromoallyl telechelic PIB, indicating the absence of side reactions affecting the chain length in the corresponding substitution reactions.