GOLD(III) CATALYZED OXIDATION OF SULFIDES TO SULFOXIDES BY NITRIC ACID UNDER PHASE-TRANSFER CONDITIONS: A NEW SYNTHESIS OF SULFOXIDES

Article abstract of DOI:10.1016/S0040-4020(01)91563-7

Gold(III) halides catalyze the oxidation of sulfides to sulfoxides in a phase-transfer process.The organic sulfides, dissolved in nitromethane, are treated with (Bu4N(1+)*AuCl4(1-)) in catalytic amount and aqueous nitric acid wich acts as an oxidant.The oxidation of the thio-group is selective and can be carried out also in the presence of other oxidizable groups, such as vinyl, tertiary amino, hydroxy, diol etc, which are left unchanged.Moreover in the case of asymmetric disulfides the reaction is regiospecific leading to the fomation of a single monosulfoxide.