High-yield synthesis of nitriles by oxidation of aldehyde N,N- dimethylhydrazones with dimethyldioxirane

Article abstract of DOI:10.1016/S0040-4039(98)00118-X

Using dimethyldioxirane, the selective transfomation of aldehyde N,N-dimethylhydrazones into the corresponding nitrites was achieved in high yield and under mild conditions. The determination of the substituent effect on rates, along with an estimate of the primary kinetic isotope effect using PhCH=NNMe₂ and PhCD=NNMe₂ provided useful hints concerning the reaction mechanism. II was also observed that the nitrile products do not undergo further oxidation, even with excess dioxirane.