Diselenides primary alcohols

It is possible to oxidize an alcohol in the presence of sulfur- or selenium-containing groups (equation 16) using r-butyl hydroperoxide and a diselenide as the oxidizing system (this also oxidizes secondary alcohols, see later).Selenium chemistry can also be used to oxidize benzylic and related primary alcohols to the aldehydes without oxidizing pyridyl (18 equation 17) or thiophenyl (19 equation 18) groups. ... 

Alkyl selenocyanates diselenldes. Primary alcohols are converted by the reagent into alkyl selenocyanates in about 80% yield. If the reaction mixture is treated with 5% KOH in CH3OH for 2 hours the alkyl selenocyanates are transformed to dialkyl diselenides (about 70% yield). The reagent converts secondary alcohols into selenocyanates and to a lesser extent into isoselenocyanates. It does not react with tertiary alcohols. 

Oxidation of alcohols. Alcohols can be oxidized to carbonyl compounds by f-butyl hydroperoxide (slight excess) and a diaryl diselenide (0.1-0.5 equiv.). Diphenyl diselenide is satisfactory, but bis(2,4,6-trimethylphenyl) diselenide is generally more satisfactory. The method is particularly efficient for benzylic and primary allylic alcohols (12 hours, 87-100% yield) oxidation of saturated alcohols, primary and secondary, requires 4-17 hours, but still proceeds in excellent yield. 

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