4-Nitroperbenzoic acid

The 4-nitroperbenzoic acid (98-99%) is available from K and K Laboratories and Prolabo (France) or may be prepared from 4-nitro-henzoic acid as described. ... 

Thus, Mathis et al. [1, 2] investigated oxidation reactions with 4-nitroperbenzoic acid, sodium hypobromite, osmium tetroxide and ruthenium tetroxide. Hamann et al. [3] employed phosphorus oxychloride in pyridine for dehydration. However, this method is accompanied by the disadvantages that the volume applied is increased because reagent has been added and that water is sometimes produced in the reaction and has to be removed before the chromatographic separation. 

The 1-hydroxyindoles (78 R = Ph, 2-pyridyl, C02Me) are rapidly oxidized by 4-nitroperbenzoic acid to the corresponding isatogens (79).18,47 The exploitation of this synthesis awaits the development of efficient general syntheses of 78. Recently an electrochemical method has been described.51 52... 

During the course of a kinetic study on the oxidation of tnuu-stilbene with peroxyphosi oric acid (HsPOs), Ogata and coworkers observed the unexpected oxidation of the reaction solvent tetrahydrofuran to y-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. 7 At room temperature, reaction times of 4-16 h are necessary. However, primary and secondary alcohols are readily oxidized under these conditions. 

Nitroperbenzoic acid has been used for the preparation of the epoxide (116 equation 42). In the aldehyde (115), the tetrasubstituted C(l)—C(2) double bond is not epoxidized since it is deactivated by conjugation with the aldehyde group, llie disubstituted double bond is not sufficiently reactive due to the inductive effect of the allyl ether moieties. The epoxidadon takes place from the a-face since the P-face is blocked by the allylic substituents. The epoxide (116) cannot be prepared in satisfactory yields using MCPBA. 

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