Anna C. Greene and Robert B. Grubbs Synthesis and evaluation of an ester-functional alkoxyamine for nitroxide-mediated polymerization Journal of Polymer Science Part A: Polymer Chemistry 47
An ester-functional alkoxyamine (2) was synthesized by the addition of two equivalents of 1-(4-(methoxycarbonyl)phenyl) ethyl radical across the nitroso group of 2-methyl-2-nitrosopropane and was found to be an effective initiator for the polymerization of styrene, isoprene, and n-butyl acrylate. Basic hydrolysis of the alkoxyamine ester groups and subsequent esterification with 1-pyrenebutanol provided the pyrene-labeled initiator (4) which was used to probe nitroxide retention after polymerization with styrene. High retention of nitroxide (>95%) was confirmed to high conversion of polymer (80%).
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