9-Azanoradamantane N-oxyl, Nor-AZADO
9-Azanoradamantane N-oxyl (Nor-AZADO) is a less hindered nitroxyl radical, that exhibits an enhanced reactivity compared with TEMPO.
A nitroxyl-radical-catalyzed oxidation using diisopropyl azodicarboxylate (DIAD) allows the conversion of various primary and secondary alcohols to their corresponding aldehydes and ketones without overoxidation to carboxylic acids. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.
M. Hayashi, M. Shibuay, Y. Iwabuchi, J. Org. Chem., 2012, 77, 3005-3009.
A series of α-diketones were readily prepared by the nitroxyl-radical-catalyzed oxidation of silyl enol ethers using magnesium monoperoxyphthalate hexahydrate (MMPP • 6 H2O) as the co-oxidant.
M. Hayashi, M. Shibuya, Y. Iwabuchi, Synlett, 2012, 23, 1025-1030.