Generation of α-Nitroalkyl Radicals by Oxidation of Nitronate Anions with Cerium(IV) Ammonium Nitrate and Their Addition Reaction to Electron-Rich Olefins

Article abstract of DOI:10.1246/cl.1995.987

α-Nitroalkyl radicals are generated by oxidation of nitronate anions with cerium(IV) ammonium nitrate.When the reactions are carried out in hte presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals proceeds to afford β-nitroketones, which are further converted to α,β-unsaturated ketones in good yield.