Oxidation products of N-substituted imines and ketone hydrazones in the presence of sodium in ether: new and convenient syntheses of diimines and substituted aryl diazomethanes

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Abstract
Several diimines have been synthesised from the reaction of substituted imines with sodium in dry ether followed by bubbling in oxygen and subsequent protonation. A probable mechanistic route for the formation of products through the dimerisation of initially formed anion radicals is presented and an alternative route, through the dimerisation of radicals formed by hydrogen abstraction from starting imine, has been excluded by substituent labelling experiments. Ketone hydrazones on treatment with sodium in ether and subsequent air oxidation gave substituted diazomethanes in excellent yields (88–95%).

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