Electrochemical conjugate additions of the allyl groups in substituted allyl halides to .ALPHA.,.BETA.-unsaturated esters.
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概要
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Electrolysis of allyl halides and diethyl fumarate (<B>2</B>) in <I>N</I>,<I>N</I>′-dimethylformamide containing 0.2 M<SUP>†</SUP> tetraethylammonium tosylate gave a conjugate addition product, ethyl 3-(ethoxycarbonyl)-5-hexenoate, in a moderate yield. The electrochemical reaction of 1-chloro-3-methyl-2-butene (<B>4</B>) with <B>2</B>, that of allyl chloride <B>4</B> with methyl crotonate (<B>6</B>), and that of methyl 4-halo-2-butenoate with <B>2</B> likewise gave the corresponding conjugate addition products, ethyl 3-(ethoxycarbonyl)-6-methyl-5-heptenoate, methyl 3,4,4-trimethyl-5-hexenoate, and ethyl 3-(ethoxycarbonyl)-4-(methoxycarbonyl)-5-hexenoate, respectively. The addition reaction of <B>4</B> to <B>2</B> takes place at the α-carbon terminus of <B>4</B> exclusively, whereas the addition of <B>4</B> to <B>6</B> at the γ-carbon terminus of <B>4</B>. These regioselectivities of the additions and pathways of the reactions are discussed.
- 公益社団法人 日本化学会の論文
著者
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Suginome Hiroshi
Department of Chemistry, Faculty of Science
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Satoh Shohei
Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University
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Tokuda Masao
Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University
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Suginome Hiroshi
Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University
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