Oxidation of Amides, Hydrazides, and Nitriles

The oxidation of amides, when it takes place at carbon atoms not adjoining the nitrogen atom, is discussed in the section Oxidation of the Carbon Chain of Amines see equations 516-518). 

The oxidation of primary amides with lead tetraacetate gives isocyanates, when carried out in dimethylformamide carbonates, when carried out in the presence of alcohols and ureas, when carried out in the presence of amines (equation 482) [1182]. 

Hydrazides are converted into aldehydes by potassium ferricyanide in 

Unsaturated nitriles are epoxidized with hydrogen peroxide- Tetra-cyanoethylene, after treatment with 30% hydrogen peroxide in acetonitrile at 10-12 °C, furnishes tetracyanoepoxyethane in 59-68% yield [750]. A similar treatment of acrylonitrile gives a 62% yield of glycidamide (epoxy-propionamide) [747]. 

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