Regioselective preparation of allylic sulfones by palladium-catalyzed reactions of allylic nitro compounds with sodium benzenesulfinate.
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概要
- 論文の詳細を見る
Treatment of allylic nitro compounds with sodium benzenesulfinate in the presence of 5 mol% of Pd(PPh<SUB>3</SUB>)<SUB>4</SUB> in <I>N</I>,<I>N</I>-dimethylformamide (DMF) at 20–70 °C for 1–10 h resulted in the formation of allylic sulfones with predominance of kinetically controlled products. The product distribution is mainly controlled by the electronic nature of substituents of an allyl unit, and the isomerization to the thermodynamically-stable isomers is negligible. On the other hand, the palladium-catalyzed sulfonylation of allylic acetates with sodium benzenesulfinate is accompanied by the isomerization to give the thermodynamically-controlled products selectively. These results can be explained by assuming that allylic nitro compounds are more reactive to the palladium catalyst than allylic acetates and sulfones.
- 公益社団法人 日本化学会の論文
著者
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Ono Noboru
Department Of Chemistry Faculty Of Science Ehime University
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KAKIHANA Masato
Department of Chemistry, The National Defense Academy
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Kawai Takashi
Department Of Agronomy Faculty Of Agriculture Tottori University
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Kaji Aritsune
Department of Chemistry, Faculty of Science, Kyoto University
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Tamura Rui
Department of Chemistry, Faculty of Science, Kyoto University
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Tamura Rui
Department of Chemistry, The National Defence Academy
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Hamamoto Isami
Department of Chemistry, Faculty of Science, Kyoto University
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Kawai Takashi
Department of Chemistry, Faculty of Science, Kyoto University
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Kakihana Masato
Department of Chemistry, The National Defence Academy
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