Potassium N-Iodo p-Toluenesulfonamide (TsNIK, Iodamine-T): A New Reagent for the Oxidation of Hydrazones to Diazo Compounds

A new reagent for the oxidation of hydrazones to diazo compounds is described. N-Iodo p-toluenesulfonamide (TsNIK, iodamine-T) allows the preparation of -diazoesters, -diazoamides, -diazoketones and -diazophosphonates in good yield and in high purity after a simple extractive work-up. -Diazoesters were also obtained in high yield from the corresponding ketones through a one-pot process of hydrazone formation/oxidation.