Abstract
The oxidation of organic sulfoxides to sulfones with sodium hypochlorite catalyzed by (salen)Mn III complexes in 90% acetonitrile–10% water (v/v) follows an overall second-order kinetics, first-order each in the oxo complex and the substrate. The less nucleophilic sulfoxides are more sensitive to substituent effect ( ρ = −2.57) compared to the corresponding sulfides ( ρ = −1.85). A positive ρ-value ( ρ = 0.50) is observed in the oxidation of phenyl methyl sulfoxide by substituted oxo(salen)manganese(V) complexes. Substituent, acid and solvent effect studies reveal the operation of a common S N2 mechanism. Correlation analyses establish that there is an inverse relationship between reactivity and selectivity in both the sulfoxide and complex series. A valid reactivity–selectivity principle (RSP) is observed in this redox system.
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