Oxidative Generation of 1-Nitroalkyl Radicals and Their Addition Reaction to Olefins.
N Arai, K Narasaka
Index: Arai, Noriyoshi; Narasaka, Koichi Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 10 p. 2525 - 2534
Full Text: HTML
Citation Number: 24
Abstract
1-Nitroalkyl radicals are generated by oxidation of potassium salt of 1-aci-nitroalkanes with ammonium hexanitratocerate (IV). When the oxidation is carried out in the presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals onto the olefins proceeds to afford β-nitro ketones, which are further converted to α, β-unsaturated ketones in high yield. Stereoselective construction of fused ring systems is achieved by ...
Related Articles:
Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives
[Kikuchi, Satoshi; Yoshida, Shunsuke; Sugawara, Yuudai; Yamada, Wataru; Cheng, Hau-Man; Sekine, Kohei; Iwakura, Izumi; Ikeno, Taketo; Yamada, Tohru Bulletin of the Chemical Society of Japan, 2011 , vol. 84, # 7 p. 698 - 717]
[Endo, Kohei; Hirokami, Munenao; Shibata, Takanori Synlett, 2009 , # 8 p. 1331 - 1335]
[Yamaguchi, Jun-ichi; Yamamoto, Shiori; Takeda, Takeshi Chemistry Letters, 1992 , # 7 p. 1185 - 1188]
[Takeda, Takeshi; Ando, Kazuo; Fujiwara, Tooru Chemistry Letters, 1983 , p. 1285 - 1288]