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Polyfunctional chloroformates were applied to the polymerization of 2-phenyl-2-oxazoline and 2-methyl-2-oxazoline. The use of a trifunctional initiator, viz. the chloroformate of 2,2-bis(hydroxymethyl)-1-butanol, led to three-arm star polymers of 2-oxazolines. Two macromolecular initiators, viz. poly(ethylene oxide) with two chloroformate end groups (α-chloroformyl-ω-chloroformyloxypoly(oxyethylene)) with number-average molar masses 350 g/mol ≤ Mn ≤ 6000 g/mol and α-chloroformyl-ω-methoxypoly(oxyethylene) with Mn = 350 and 750 g/mol were applied for the synthesis of poly(2-oxazoline)-block-poly(ethylene oxide)-block-poly(2-oxazoline) and poly(2-oxazoline)-block-poly(ethylene oxide) copolymers, respectively.