Conversion of Aldehydes into Nitriles via Oxidation of Their Dimethylhydrazones

Abstract

The 3-chloroperoxybenzoic acid oxidation of dimethylhydrazones of aromatic aldehydes gives the corresponding nitriles in good yields. Two further examples of the same oxidative transformation of cinnamaldehyde and of hexanal are also given. Except for hexanal hydrazone, all other aldehyde hydrazones can also be efficiently converted into nitriles by treatment with methanolic 30 % hydrogen peroxide in the presence of catalytic amounts of selenium dioxide or, preferentially, 2-nitrobenzeneseleninic acid.