78998-77-3

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• 1666-13-3 diphenyl diselenide 
• 78998-74-0 6-(phenylseleno)-5-decanol 

Relevant academic research and scientific papers

Halogen and chalcogen cation pools stabilized by DMSO. Versatile reagents for alkene difunctionalization

Halogen and chalcogen cations (X+ = Br+, I +, ArS+, and ArSe+) were generated by low-temperature electrochemical oxidation in the presence of dimethyl sulfoxide (DMSO) and were accumulated in the solution. DFT calculations indicated that DMSO stabilizes these cations by coordination. The complexes of I+ with one and two DMSO molecules were observed by cold-spray-ionization MS analyses. The stability of the resulting cation pools of X+ increased in the order of Br+ + + +, which could be explained in terms of the electronegativity of X. The cation pools served as versatile reagents for organic synthesis; the reactions with alkenes gave β-X-substituted alkoxysulfonium ions, which were converted to the corresponding carbonyl compounds by the treatment with triethylamine, whereas the treatment with methanol gave the corresponding alcohols. The reactions with aminoalkenes and 1,6-dienes gave the cyclized products.

Oxidation of Alcohols with tert-Butyl Hydroperoxide and Diaryl Diselenide

Treatment of alcohols with tert-butyl hydroperoxide in the presence of diaryl diselenide in refluxing benzene gives the corresponding aldehydes or ketones.Although some allylic alcohols undergo oxidation in the presence of 10-15 mol percent of bis(p-chlorophenyl) diselenide, use of 0.5 equiv of bis(2,4,6-trimethylphenyl) diselenide gives satisfactory results in almost all cases.The procedure can be used for selective oxidation of alcohols bearing a phenylthio or phenylseleno group, which usually survives the reaction conditions to give the corresponding carbonyl compounds.

SELECTIVE OXIDATION OF HYDROXY GROUPS OF PHENYLTHIO AND PHENYLSELENO ALCOHOLS

Various kinds of alcohols bearing phenylthio or phenylseleno moiety were converted into the corresponding carbonyl compounds in good to excellent yields by treating with dimesityl diselenide and tert-butyl hydroperoxide.