Reactions of benzyne with substituted benzenes.
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概要
- 論文の詳細を見る
The reactions of benzyne with substituted benzenes (anisole, chlorobenzene, methyl benzoate, benzylidyne trifluoride and toluene) giving the Diels-Alder adducts were investigated, where two positionally isomeric adducts were possible, <I>i.e.</I>, a geminal-para adduct (1,4-adduct with respect to the substituent) and an ortho-meta adduct (2,5-adduct). From the competition reactions, relative reactivities of benzyne to substituted benzenes were estimated for the 1,4-addition and 2,5-addition. Markedly different substituent effects were observed. For the 1,4-addition, large negative ρ value (−1.79) was observed, but for the 2,5-addition, substituent effect was small. From benzyne and toluene, <I>o</I>-benzylbiphenyl (<B>13</B>) and 2-benzyl-3-phenylbenzo[5,6]bicyclo[2.2.2]octatriene (<B>14</B>) were obtained as the successive "ene" products together with the normal Diels-Alder adducts.
- 公益社団法人 日本化学会の論文
著者
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Yamada Hidenori
Department Of Bioengineering Science Faculty Of Engineering Okayama University
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Yoshida Zenichi
Department Of Aeronautical Engineering Kyoto University
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Tabushi Iwao
Department of Pharmaceutical Sciences, Kyushu University
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Oda Ryohei
Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University
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Tabushi Iwao
Department oe Pharmaceutical Sciences, Kyashu University
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