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Nucleophilic Reactivities of Bleach Reagents

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journal contribution
posted on 2018-05-09, 12:18 authored by Robert J. Mayer, Armin R. Ofial
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 k2 = sN(N + E) gave the parameters N (and sN), which were applied to predict the rates of Weitz–Scheffer epoxidations.

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