Nucleophilic Reactivities of Bleach Reagents

The nucleophilicities of the oxidants hydroperoxide, hypochlorite, hypobromite, bromite, and peroxymonosulfate were determined by following the kinetics of their reactions with a series of benzhydrylium ions of known electrophilicity ( E ) in alkaline, aqueous solutions at 20 °C. The reactivities of the oxidants correlate only weakly with their basicities. Analyzing the rate constants by using the relationship log k 2 = s N ( N + E ) gave the parameters N (and s N ), which were applied to predict the rates of Weitz–Scheffer epoxidations.