Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

Diaryl diselenides and related benzisoselenazol-3(2H)-ones are presented as the catalyst for hydogen peroxide and t-butylhydroperoxide oxidation of various types of organic substrates. Most of the reactions studied in our laboratory have a practical value. The aromatic aldehydes and ketones are oxidized to arenecarboxylic acids or converted to the phenols while cycloalkanones gave cycloalkanecarboxylic acids with ring contraction. From the azomethine compounds, depending on their structure, nitriles, parent carbonyl compounds, carboxylic acids or their esters are produced. Primary benzylamines gave nitriles, while the secondary are oxidized to nitrones. Alkylarenes are oxidized to the alkylaryl ketones and alkenes to epoxides. By oxidation of 1,4-dimethoxysubstituted and some polycondensed arenes the quinones are produced. The postulated mechanisms are discussed and the methods for synthesis of the title compounds are described.