The aryl radical anion (I2) is expected to exist only at very low concentrations due to its predicted rapid reaction with RAE, as supported by DFT calculations. The viability of this step was probed by cyclic voltammetry where phthalonitrile and 4-(1methylcyclohexyl)phthalonitrile ( ) exhibit half wave potential reduction potentials (E1/2) of -2.26 V and -2.38V vs Fc/Fc + respectively (Fig ). Both species are sufficiently negative to reduce the RAE (1) as its reduction potential is -1.62 V vs Fc (Fig. ). As a result, the radical anion electron can feasibly shuttle from the anionic product (I2) to the phthalonitrile starting material, as evidenced by both the cyclic voltammetry and DFT (Fig. and Fig.