Bidentate nitrogen-ligated iodine(V) compounds, Bi(N)-HVIs, were first reported by Zhdankin and coworkers in 2002. Recently, we demonstrated that these compounds, and specifically Bi(4-CO2Etbipy)-HVI, were uniquely effective at facilitating the highly efficient double oxidative dearomatization of electron-deficient phenols, such as p-nitrophenol (Table , entries 1 and 2). In this report, the reactivity of Bi(4-CO2Etbipy)-HVI was benchmarked against a range of other iodine(V) reagents. Specifically, IBX provided very low yields of the target quinone and precursor PhI(O)(OAc)2 gave no reaction at all (entries 3 and 4). The stronger oxidant PhI(O)(OTf)2 afforded the product quinone in 59% yield after 20 minutes, which decreased to 27% yield after 4 hours due to continued oxidative degradation (entries 5 and 6).