also with KO t Bu in THF and observed the formation of tert-butoxinitrobenzene. Following Janzen's original reasoning, they propose that the obtained product proceeds via the formation of [1 •-]. The process is initiated by a nucleophilic attack of the base to [1], followed by the deprotonation of this anion intermediate by another base, and finalised by the reduction of two [1] molecules by the dianion, as summarised by reactions 1, 5 and 6 in their work. Note that their reasoning was based on indirect evidence as no EPR characterization of the proposed species was provided. Our DFT calculations with NaO t Bu predict a barrier of 15 kcal/mol for the nucleophilic attack, followed by a highly impeded subsequent deprotonation by a second base molecule and a highly exothermic final reduction product (Scheme S58 top) -a similar profile, with smaller barriers, is maintained when the Na + ion is removed (Scheme S58 bottom), but this would imply a full dissociation of the salt, in contrast to its known tendency to form clusters in THF. Additionally, this mechanism would result in the formation of tert-butoxinitrobenzene, but we did not observe the corresponding chemical shifts in NMR experiments (Figure ). Finally, to assess whether this mechanism could be active for other bases, we studied the first nucleophilic attack with iPr Cp -anion, finding a barrier of > 26 kcal/mol (Scheme S59), which is not competitive against the proposed direct SET at 7 kcal/mol. Thus, this mechanism is also discarded as a valid, general option in our case. Driver et al. studied the reaction of nitrostilbenes with XO t Bu in THF and observed the formation of N-hydroxyindoles or oxindoles when X = Na or K, respectively. EPR studies were employed to argue that [1 •-], in the case of NaO t Bu, and a combination of oxygen and carbon-centred radicals, in the case of KO t Bu, were the key, yet distinct, intermediates enabling product formation. However, we have shown that both alkoxides lead to the same specie (Table ). Despite Driver's impressive results, this discrepancy might arise from their broad EPR linewidths, which hamper resolution of all HFCs, as well as a lack of mechanistic insight guided by computational studies. Another stark difference is the reported absence of reaction progress when using LiO t Bu, in contrast to our results that clearly demonstrate [1 •-][Li + ] formation under these conditions. To the best of our knowledge, this is the most closely related work to our results, but here we provide an unequivocal characterisation and clear formation mechanism of [1 •-]([X + ]) under a broader set of conditions.