The peroxy radical complexed to a lithium cation has been used to model electrostatic catalysis in the oxidation of methane to methanol and the epoxidation of ethylene in nb initio molecular orbital calculations. Both reactions are found to proceed in two steps. The first steps of both reactions, hydrogen abstraction from methane and addition to ethylene, respectively, are conventional and enjoy both a kinetic and a thermodynamic advantage from complexation to the metal cation. The second step is in each case the cleavage of the O-O bond of the peroxide formed, This type of reaction is found to be remarkably facile in metal ion complexed peroxides and proceeds by a classical backside attack mechanism. For both reactions investigated, the metal ion complexation provides considerable assistance for the forward reaction. Analogies to iron-catalyzed biological oxidations are drawn, and suggestions of possible consequences for their reaction mechanisms are made.