The systematical kinetic investigations of four 2-substituted-2-oxazoline monomers with four initiators at two temperatures and four monomer/initiator ratios are described. To cover this broad range of variables (128 different combinations), an automated synthesizer was used to accelerate the investigations and to provide highly comparable results. With both gas chromatography and gel permeation chromatography, the livingness and the polymerization rates were determined for the different polymerizations. The resulting insights in the kinetics were used for the directed synthesis of truly random copolymers and copolymers with composition drift. (C) 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 1830-1840, 2004.