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 = s( N + E) gave the parameters N (and s), which were applied to predict the rates of Weitz-Scheffer epoxidations.