Fig. 2: Control experiments for mechanistic study.
From: Birch reductive arylation by mechanochemical anionic activation of polycyclic aromatic compounds
a Comparison with the solution-state reactions. b High-concentrated reactions in the solution-state. c Stepwise in-solution and in-solid state reaction. d Deuteration experiment in the reaction with ethylenediamine by quenching D2O. e Deuteration experiment in the reaction with THF by quenching D2O. f Reaction from dihydroanthracene 1b. g Side reaction from fluorobenzene. h Cyclization of 1-(3-buten-1-yl)−2-fluorobenzene suggesting generation of anion radical. i Control reaction of anthracene with 1-(3-buten-1-yl)−2-fluorobenzene. j Plausible pathways of Birch reductive arylation.
