Stable free radical polymerization––acrylate alkoxyamine synthesis

An efficient synthesis of the alkoxyamine containing a benzoyl peroxide fragment, one tert-butyl acrylate monomer unit and TEMPO via an oxymercuration reaction followed by an oxidative demercuration reaction is reported. The formation of significant amounts of an undesired reduced product with the latter reaction was overcome by using a milder reducing agent (NaBH3CN) than those (NaBH4, LiBH4) reported to work well in other systems.