Given the abundant literature precedent showing [1 •-]([X + ]) formation using alkali metals (X=Li, Na, K, Rb, Cs) and the fact that the nitro group can act as a Lewis acid, we wondered whether we could induce nitrobenzene reduction using other types of reactants. The choice of anionic organic bases (B -X + ) seemed appropriate, given that they provide the alkali-metal counterion (X + ) to form the needed ion-pair, while also offering a readily available lone pair as a source of electrons (B -). In particular, we used tertbutyllithium ( t BuLi), lithium diisopropylamide (LDA), lithium tert-butoxide (LiO t Bu), sodium tertbutoxide (NaO t Bu), potassium tert-butoxide (KO t Bu), lithium bis(trimethylsilyl)amide (LiHMDS), sodium bis(trimethylsilyl)amide (NaHMDS), potassium bis(trimethylsilyl)amide (KHMDS), and sodium isopropyl cyclopentadienide (Na iPr Cp) bases in pure polar (tetrahydrofuran, THF) and apolar (benzene, C 6 H 6 ) solvents, as well as their combination with dimethyl sulfoxide (DMSO) in varying mixing ratios (Scheme 1).