The Substituent Effect on the Addition Course of the Diels-Alder Reaction of 2-Methyl-5-substituted-1,4-benzoquinones with Butadiene

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概要

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• The substituent effect on the addition course of the Diels-Alder reaction of butadiene with 2-methyl-1,4-benzoquinones which carry the cyano(V), dimethylcarbamoyl(VI), β-ethoxycarbonylethyl(VII), β-cyanoethyl(VIII), ethoxycarbonyl-trans-vinyl(IXa) group at the C_5 position, respectively, was examined. The addition of V and VI occurred one-sidedly at the ethylene linkage carrying the electronwithdrawing cyano and dimethyl-carbamoyl group. In the compound (VII and VIII), butadiene added at both ethylene linkages giving a mixture of adducts in the ratio of XXXIIa/XXXIIb=2/3 and XXXIIIa/XXXIIIb=1/1,respectively. The reaction of 2-methyl-5-(ethoxycarbonyl-trans-vinyl)-1,4-benzoquinone(IXa) with butadiene furnished the adduct (XXXIVa), indicating that the addition occurred at the ethylene linkage bearing the unsaturated ester group.

• 公益社団法人日本薬学会の論文
• 1973-01-25

著者

• 原山 尚

  Faculty of Pharmaceutical Sciences, Chiba University

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 原山 尚

  Faculty Of Pharmaceutical Sciences Kyoto University

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

• 沖 正信

  Faculty Of Pharmaceutical Sciences Kyoto University

• 大谷 光昭

  Shionogi Research Laboratories Shionogi & Co. Ltd.

• 大谷 光昭

  Faculty of Pharmaceutical Sciences, Kyoto University

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