A Kinetic Study of Sulfide Oxidation by Sodium Hypochlorite Using Phase-Transfer Catalysis

Article abstract of DOI:10.1021/ja00193a029

The use of sodium hypochlorite as a synthetically useful oxidizing agent is reported for the oxidation of lipophilic organic sulfide substrates employing phase-transfer catalysis (PTC).The PTC results in nearly complete oxidation of the substrate in 20 min, with high selectivity to the sulfoxide, compared to 5 h in its absence.Kinetic studies show the reaction occur via transfer of OCl^- into the organic phase.Under certain conditions the transfer is rate limiting.The addition of a transition-metal catalyst (TPPMnCl) further increased the rate and led to the complete conversion of the sulfide to the sulfone, illustrating that NaOCl(aq) is a potent oxidizing agent in these biphasic systems.