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.
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Fang, XQ., Liu, YC., Wang, GW. et al. A novel coenzyme NADH model 1-benzyl-1,4-dihydronicotinamide-mediated reaction: a single intermediate serves two mechanisms. Res Chem Intermed 32, 603–611 (2006). https://doi.org/10.1163/156856706778400316
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DOI: https://doi.org/10.1163/156856706778400316