Selective oxidation of unsymmetrical thiosulfinic S-esters to the corresponding thiosulfonic S-esters with NaIO4.
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Unsymmetrical thiosulfinic <I>S</I>-esters were oxidized with sodium metaperiodate in aqueous media to the corresponding unsymmetrical thiosulfonic <I>S</I>-esters nearly quantitatively. The oxidation was accelerated by addition of a catalytic amount of inorganic and organic acids or halogen. Sulfinic esters were produced competitively along with the thiosulfonic <I>S</I>-esters in the oxidation of thiosulfinic <I>S</I>-esters in aqueous alcohol. However, unsymmetrical disulfides were not oxidized selectively to the corresponding unsymmetrical thiosulfonic <I>S</I>-esters but a mixture of both symmetrical and unsymmetrical thiosulfonic testers was obtained.
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