Reduction of mononitroarenes by hydroxide ion in water catalyzed by β-cyclodextrin: enhanced reactivity of hydroxide ion

Ordinarily the reducing ability of HO− in water is extremely low as a result of its stabilization by hydration. Reductions by hydroxide ion have only been observed previously in aprotic organic solvents. We find that several mononitroarenes are reduced to azoxyarenes by NaOH in water in the presence of β-cyclodextrin. HO− acts as a one-electron reductant with enhanced reactivity.