Reduction by a model of NAD(P)H. 36. First and direct evidence for the multi-step mechanism.
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概要
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Reductions of thiobenzophenone derivatives with a model compound of NAD(P)H, 1-benzyl-1,4-dihydronicotinamide (BNAH) or <I>N</I>-(α-methylbenzyl)-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide (Me<SUB>2</SUB>PNPH), in a solvent containing an <I>O</I>-deuterated alcohol afforded products partially deuterated at their methine positions. The deuterium content depends both on the character of substituents in the substrate and on the polarity of solvent. In contrast, no incorporation of deuterium into the product was observed in the reduction of thiopivalophenone with BNAH or Me<SUB>2</SUB>PNPH under the same conditions. These results can be accounted for in terms of an electron transfer followed by a proton transfer from the model to substrate. This is the first and direct evidence for the ion radical-pair intermediacy for reductions by model compounds of NAD(P)H.
- 公益社団法人 日本化学会の論文
著者
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Ohno Atsuyoshi
Institute For Chemical Research Kyoto Univ.
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Nakamura Kaoru
Institute For Chemical Research Kyoto University
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Oka Shinzaburo
Institute For Chemical Research Kyoto University
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Yasui Shinro
Institute for Chemical Research, Kyoto University
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