The reactivity–selectivity principle in the oxidation of aryl methyl sulfides with sodium hypochlorite catalysed by (salen)MnIII complexes

Abstract

The kinetics of oxygen atom transfer from four oxo(salen)manganese(V) complexes to various para-substituted phenyl methyl sulfides have been studied spectrophotometrically in 90% acetonitrile-10% water(v/v) at 20oC. Electron-releasing substituents in sulfides and electron-withdrawing substituents in oxo(salen)manganese(V) complexes enhance the rate of oxidation. Correlation analyses establish that there is an inverse relationship between reactivity and selectivity in both the sulfide and the complex series. Mathematical treatment of the results shows the operation of a valid reactivity-selectivity principle in this redox system.