Oxidation of Secondary Alcohols to a-Hydroxy Hydroperoxides

A unique reaction leading to unique compounds takes place when secondary alcohols are treated with oxygen in the presence of benzophe-none as a sensitizer for photooxidation. The products, which are isolated by distillation at room temperature at 0.1-0.8 mm of Hg in 16-25% yields, show the presence of active oxygen and react with 2,4-dinitrophenylhy-drazine to form 2,4-dinitrophenylhydrazones of the corresponding ketones. 

The compounds must be handled with utmost care because they tend to explode (equation 269) 44.  

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