Bis (
p-methoxyphenyl) selenoxide, readily available from anisole and selenium dioxide or selenium oxychloride, is of practical use as a tractable and versatile oxidizing agent. Thus it can be used for mild oxidations of thiol to disulfide, sulfide to sulfoxide, hydroquinone to
p-benzoquinone, catechol to
o-benzoquinone, phosphine to phoshine oxide, benzoylhydrazine to
sym- dibenzoylhydrazine, phenylhydroxylamine to azoxybenzene, and benzoin to benzil. Its specific reactivity is demonstrated by a useful conversion of thioamides involving thioureas into 1, 2, 4-thiadiazoles. In particular, polymer-supported analogous selenoxide effects novel solvent-dependent reactions toward thioamides. In addition, the title selenoxide has potential applicability such as an effective reagent for Kornblum reaction, a cooxidant for catalytic SeO
2 oxidation, and a mediator for electrochemical oxidation.
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