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New Selective Oxidation of Unsymmetrical Thiolsulfinates to the Corresponding Thiolsulfonates with Sodium Metaperiodate by Yong Hae Kirn; Toshikazu Takata; Shigeru Oae is a Chemistry article available to read on EtoBox.

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We have recently reported that oxidations of unsymmetrical thiolsulfinates with peroxy acid 1) or dinitrogen tetraoxide 2) afforded the corresponding symmetrical thiolsulfonates which were undoubtedly derived by the cleavage of sulfur-sulfur bond. We now have found that both aryl-and alkyl unsymmetrical thiolsulfinates are oxidized selectively with sodium metaperiodate in aqueous media to the corresponding unsymmetrical thiolsulfonates quantitatively. The oxidation was accelerated by addition of a catalytic amount of inorganic or organic acid as well as iodine 3)(Table II). Since thiolsulfinates are generally unstable and known to disproportionate readily to the corresponding disulfides and thiolsulfonates 4) , only a sporadic studies on the oxidation of thiolsulfinate have been carried out 11215) and showed that all these oxidations involve the cleavage of sulfur-sulfur bond and gave the corresponding thiolsulfonates. However, surprisingly, with an equimolar amount-of NaI04 all these unsymmetrical thiolsulfinates were selectively oxidized to the corresponding unsymmetrical thiolsulfonates in aqueous solvent such as water-dioxan, acetonitrile or acetic acid under mild conditions(ca

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Author

Yong Hae Kirn; Toshikazu Takata; Shigeru Oae

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1978

Language

EN

Field

Chemistry (Physical Sciences)