Peroxyphosphoric acid ethers

During the course of a kinetic study on the oxidation of tran.r-stilbene with peroxyphosphoric acid (H3PO3), Ogata and coworkers observed the unexpected oxidation of the reaction solvent tetr ydrofuran to 7-butyrolactone. However, although n-butyl ether was also oxidized by this reagent, tetrahydropy-ran and dioxane were apparently inert. Ethers undergo oxidation on treatment with 4-nitroperbenzoic acid in chloroform. Moderate yields of esters and lactones are obtained when simple ethers are treated with calcium hypochlorite. At room temperature, reaction times of 4-16 h are necessary. However, primary and secondary alcohols are readily oxidized under these conditions. 

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