Because the dimerization of the alkoxide bases renders the overall process slightly endothermic, we also investigate hydrogen atom transfer (HAT) reactions from the solvent molecules ((2.2) in Figure , Scheme S25-S33), as these are typical mechanisms invoked for O t Bu• and HMDS• 12 radicals. The disappearance of the resulting radical-containing solvent molecule from the medium is assumed to occur via a highly exothermic dimerization (Scheme S49-S51). We find that for both radical bases, THF preferentially favours HAT over benzene and that subsequent solvent dimerization favours the process (Table ). However, as for the base dimerization, we were unable to detect the dimerised solvent molecules in either 1 H DOSY NMR (Figure & S49) or 2 H NMR (Figure ). Still, we believe that the presented computational results validate this mechanism.