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Mayer, Robert J.; Ofial, Armin R. (2018): Nucleophilic Reactivities of Bleach Reagents. In: Organic Letters, Vol. 20, No. 10: pp. 2816-2820
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Abstract

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 degrees 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.