Polymer-supported oxygen atom transfer reagents have been reported in the literature, but can a biodegradable one be synthesized? This work describes a novel cyclic carbonate monomer with a pendant iodoarene that can be polymerized with common organocatalytic ring-opening polymerization catalysts. Polycarbonate backbones are biodegradable. In addition to preparation of the homopolymer, the iodoarene monomer could be randomly copolymerized in small molar ratios (10%, 25%, and 40%) with a well-known cyclic carbonate monomer tethered to a pendant benzyl group. The iodoarene groups of the polymers were oxidized to the desired oxygen atom transfer reagent, an iodosylarene, using potassium chlorate and sodium hydroxide. The polymers were tested for their ability to transfer oxygen atoms to common substrates like phosphines, and attempts to recycle the polymers after the oxidation reactions are described.

Synthesis and reactivity of biodegradable, polymer-supported oxygen atom transfer reagents

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