Part 10: chemically triggered alkoxyamine C–ON bond homolysis in ionic liquid solvents

Abstract

The homolysis of the C–ON bond of three alkoxyamines – the non-activated alkoxyamine 1, its N-methylated version 2 and its N-oxidated version 3 – is investigated in several ionic liquids. These three alkoxyamines were selected as their homolysis is prone to sharp solvent effects. EPR studies on these alkoxyamines in four ionic liquids (IL) afforded results that were similar to those previously published (Polymer. Chem., 2012, 3, 2901; J. Org. Chem., 2012, 77, 9634). Indeed, the correlations between Reichardt solvent polarity constants E^N_T and log k_d, and those based on the Kalmet–Abboud–Taft relationship did not change significantly when ILs were implemented.