To develop a constant poten al single-pass flow reactor, the Shono oxida on was chosen as a model reac on. This reac on has been shown in other flow reactors to either produce a mixture of singly and over oxidized products as a result of poor mass transfer at the surface of the electrode, or suffer from low conversion. Choosing a reac on that is sensi ve to overreac on was ideal for developing a general strategy for understanding how to simultaneously op mize rate and selec vity. Addi onally, from a synthe c viewpoint the Shono oxida on is a powerful method for func onaliza on of saturated nitrogen containing heterocycles via the "ca on-pool" method popularized by Yoshida and coworkers . Mechanis cally this reac on is thought to proceed via the single electron oxida on of an amide or carbamate (Figure ). The radical ca on intermediate is much more acidic than the neutral compound and undergoes deprotona on to form an alpha-radical which is subsequently oxidized a second me to form an iminium ion. Ul mately, the iminium ion is trapped by an alkoxide to form the desired product.