Novel functional initiators for oxazoline polymerization

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Abstract
The initiating behavior of the functional tosylates 1–4 and triflates 5 and 6 for the cationic ring‐opening polymerization of 2‐methyl‐1,3‐oxazoline was investigated. The emphasis was directed at tosylates and triflates with 2,2‐dimethyl‐1,3‐dioxolane‐, 2,3‐epoxypropyl‐, 2,3‐didodecanoyl‐glycerol‐, and cholest‐5‐en‐moieties that allow the construction of amphiphilic polyoxazoline conjugates. The tosylates were prepared by a simple reaction of the corresponding alcohols with p‐toluenesulfonyl chloride, whereas the preparation of the corresponding triflates required low temperature and the use of 2,6‐di‐tert‐butylpyridine as a sterically hindered base. Among the initiators tested, 2,2‐dimethyl‐(4‐trifluoromethanesulfonyloxymethyl)‐1,3‐dioxolane 6 gave the best results in respect to molecular weight and polydispersity. Starting from the corresponding functional oxazoline polymers obtained with 6 as an initiator, amphiphilic lipid‐polyoxazoline conjugates with a diacylglycerol backbone could be prepared. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 2821–2831, 2001

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