A novel coenzyme NADH model 1-benzyl-1,4-dihydronicotinamide-mediated reaction: a single intermediate serves two mechanisms |
| |
| Authors: | Xin-Qiang Fang You-Cheng Liu Guan-Wu Wang Yu-Ping Ke |
| |
| Institution: | (1) Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China;(2) National Laboratory of Applied Organic Chemistry, Lanzhou, Gansu, 730000, P.R. China |
| |
| Abstract: | Thermal reaction of ethyl (2Z)-4-bromo-2-cyano-3-(2-naphthyl)but-2-enoate (BCNB) with coenzyme NADH model 1-benzyl-1,4-dihydronicotinamide (BNAH) gives
the debrominated cyclized product (E)-1-cyano-2-methyl-2-(2-naphthyl)cyclopropane-1-carboxylate (1), debrominated olefinic products ethyl (2E)-2-cyano-3-(2-naphthyl)but-2-enoate (2) and ethyl (2Z)-2-cyano-3-(2-naphthyl)but-2-enoate (3). The formation of 1 proceeds via partial concerted hydride transfer and debromocyclopropanation, whereas the formation of 2 or 3 proceeds via an electron transfer-debromination-hydrogen abstraction mechanism. Nonetheless, they all derived from the same electron-transfer
intermediate complex. |
| |
| Keywords: | Coenzyme NADH model hydride transfer electron transfer intermediate complex |
| 本文献已被 SpringerLink 等数据库收录！ |
|
