Several (protected) amine and alcohol functionalized styrene monomers were synthesized via readily accessible synthetic routes. The controlled radical copolymerization of these functionalized styrene monomers with styrene was performed using two alkoxyamines, namely N-(2-methylpropyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxylprop-2-yl) hydroxylamine (MAMA-SG1) and N-tert-butyl-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine. The copolymers obtained showed low polydispersities, controlled molecular weights, and a random topology. The thermal properties of the polymers were determined with differential scanning calorimetry. All polymers were amorphous and showed glass transition temperatures between 40 and 111 degrees C. Deprotection of the copolymers afforded amine or alcohol pendant polystyrenes which were readily functionalized with isocyanates. (c) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem50: 780-791, 2012