Table . Reported dearomatization of electron-deficient phenols to ortho-quinones by various iodine(V) reagents: selected results. decrease the product yield? Why does the use of pyridine rather than a bipyridine attenuate the reactivity of the iodine(V) reagent? We anticipated that employing Density Functional Theory (DFT) to answer the foregoing questions would provide an enhanced understanding of the fundamental processes involved in iodine(V)-mediated oxidations. Furthermore, by revealing how the structure of Bi(4-CO2Etbipy)-HVI specifically relates to its function, we thought that our study could serve as a platform from which the design of new hypervalent iodine(V)