The synthesis of a monoacrylate functionalized poly(isobutylene) (PIB) macromonomer (PIBA) has been achieved by a two-step reaction starting from a commercially available PIB. Firstly, terminal olefins (vinylidene and trisubstituted olefin) of PIB were transformed to a phenolic residue by Friedel-Crafts alkylation followed by subsequent esterification of the phenol with acryloyl chloride, catalyzed by triethylamine. PIBA structure was confirmed by H-1-NMR, C-13-NMR and GPC before utilizing in the RAFT copolymerization with N,N-dimethylacrylamide (DMA) to obtain statistical copolymers (P[(DMA-co-(PIBA)]). Monomer conversions were consistently higher than 85% for both DMA and PIBA as monomer feed composition was varied. Chain extension of poly(N,N-dimethylacrylamide) with PIBA to synthesize block copolymers (P[(DMA-b-(PIBA)]) was also achieved with near quantitative monomer conversions (>97%). Block formation efficiency was not quantitative but purification of block copolymers was possible by selective precipitation. (c) 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 634-643