(ii) The overall activation barrier for the oxidative dearomatization increases in the order X = OTf < TFA < OAc. This suggests that the identity of the X-ligand is an important factor in determining the ease of the redox process. Specifically, PhI(O)(OAc)2 bearing strongly coordinating acetate ligands has a barrier of 34.5 kcal/mol, while PhI(O)(OTf)2, with weakly bound triflate ligands has a computed activation barrier of only 21.7 kcal/mol. This finding is in agreement with the experimental observations and clearly explains why PhI(O)(OTf)2 is an appropriate oxidant for the dearomatization reaction, while PhI(O)(OAc)2 gives no reaction.