Abstract
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.
Highlights
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
During the last four decades it has been reported that selenium, its dioxide and some organoselenium compounds can be used as stoichiometric oxidants or oxidation catalysts
Diaryl diselenides and benzisoselenazol-3(2H)-ones have been in the centre of our interest, because in many cases they can act more efficiently and selectively as oxygen-transfer catalysts other selenium compounds and they are useful for hydrogen peroxide and tbutyl hydroperoxide (TBHP) oxidation of variety organic compounds
Summary
During the last four decades it has been reported that selenium, its dioxide and some organoselenium compounds can be used as stoichiometric oxidants or oxidation catalysts. Diaryl diselenides and benzisoselenazol-3(2H)-ones have been in the centre of our interest, because in many cases they can act more efficiently and selectively as oxygen-transfer catalysts other selenium compounds and they are useful for hydrogen peroxide and tbutyl hydroperoxide (TBHP) oxidation of variety organic compounds. Investigation of the reactivity of areneperoxyseleninic acids has shown that the use of the compound 11 as a stoichiometric reagent for Bayer-Villiger oxidation gave results similar to those when hydrogen peroxide in the presence of a catalytic amount of its precursor diselenide 4 was an oxidant.. The results of more detailed studies on the chemo- and stereoselectivity of this reaction support the mechanism, presented for oxidation of cyclohexanone in Scheme 8 Most probably it involves addition of two bulky arylselenium cations to both α-positions of the ketone, elimination of diaryl diselenide from the adduct 26, and the rearragement of intermediate 27 into the cyclopentanecarboxylic acid.
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