GENERATION OF ALPHA-NITROALKYL RADICALS BY OXIDATION OF NITRONATE ANIONS WITH CERIUM(IV) AMMONIUM-NITRATE AND THEIR ADDITION-REACTION TO ELECTRON-RICH OLEFINS
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作者:
ARAI, N
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UNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPANUNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN
ARAI, N
[1
]
NARASAKA, K
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UNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPANUNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN
NARASAKA, K
[1
]
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[1] UNIV TOKYO, GRAD SCH SCI, DEPT CHEM, BUNKYO KU, TOKYO 113, JAPAN
alpha-Nitroalkyl radicals are generated by oxidation of nitronate anions with cerium(IV) ammonium nitrate. When the reactions are carried out in the presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals proceeds to afford beta-nitroketones, which are further converted to alpha,beta-unsaturated ketones in good yield.