Benzeneseleninic anhydride derivatives

As a result of the powerful oxidizing potential of benzeneseleninic anhydride, it is incompatible with the presence of a number of functional groups, although many common moieties are well tolerated. Thus, it has been shown to convert thiocarbonyl compounds such as xanthates, thiocarbonates, thioamides and thiones, and hydrazones, oximes, thiosemicarbazones and hydroxyhttnines, into the corresponding carbonyl compounds under relatively mild conditions. Furthermore, hydrazo derivatives are converted to the azo compounds. ... 

The use of benzeneseleninic anhydride in the conversion of thiocarbonyl compounds into the corresponding oxo-derivatives has been reported in full similar reactions were achieved using diaryl telluroxides. ° Steroidal ketones reacted with tris(phenylseleno)borane or tris(methylseleno)borane to give phenyl or methyl selenoacetals. 

Oximes, Semicarbazones, Hydrazones, and Related Derivatives.—Lead tetraacetate was used to regenerate ketones from the semicarbazones and allowed a novel synthetic approach to 18-hydroxycorticosterone from 18-hydroxy-ll-oxoprogesterone. The use of benzeneseleninic anhydride as a deprotecting agent for phenylhydrazones, semicarbazones, oximes, and related derivatives has been described in full. ... 

Benzeneseleninic anhydride (PhSe0)20 is highly recommended for the regeneration of ketones from hydrazones, oximes, and semicarbazones. Ketones have been regenerated from the same range of derivatives using a stoicheiometric amount of titanous chloride in buffered acetic acid and dioxan. ... 

Benzeneseleninic anhydride converts hydrazones, oximes, and semicarbazones into the parent ketones, and oxidizes phenols to ortho-qmnone derivatives [e.g. (80) gives (81)]. The combination of PhSe(0)0H and H2O2 accomplishes epoxidation... 

Benzeneseleninic acid or anhydride See Benzeneseleninic acid Hydrazine derivatives... 

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