Stopped-flow kinetic runs were performed on a single-mixing OLIS RSM-1000 stopped-flow spectrophotometer. The solvent was anaerobic MeCN (Burdick & Jackson low water) that was sparged with argon and plumbed directly into a N2-filled glovebox. All solutions used for kinetics were prepared in a N2-filled glovebox and used within an hour of preparation. All measurements were made at 295 ± 2 K. Typically, a solution of oxidant (10−3 to 10−5 M) was reacted with a series of solutions of 1 generated in situ with tetra-butylammonium hydroxide (1 M in MeOH). MeOH was added to solutions of 1 such that the [MeOH] was consistent in all solutions. Concentrations of 1 ranged from ca. 10- to 50-fold molar excess (in reactions using aminium oxidants) or ca. 4- to 20-fold molar excess (in reactions using ferrocenium oxidants). Additional information can be found in the Supplementary Materials.

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