Competitive cyclization in the reaction of hexafluoropropene with 2-aminobenzamide.
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概要
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The reaction of hexafluoropropene(HFP) with 2-aminobenzamide afforded 2-(1,2,2,2-tetrafluoroethyl)-4(3<I>H</I>)-quinazolinone (<B>4</B>) and <I>N</I>-(2-cyanophenyl)-2,3,3,3-tetrafluoropropionamide (<B>5</B>) in <I>ca.</I>1 : 1 ratio, which is essentially independent of the reaction temperatures ranging from room temperature to 100 °C. The formation of the two products is explained in terms of the competitive cyclization of the imidoyl fluoride intermediate, the N-6 and O-6 ring closures ultimately yielding <B>4</B> and <B>5</B>, respectively. In contrast to the HFP reaction, 2-(trifluoromethyl)pentafluoropropene (OFIB) and 2-aminobenzamide gave only the O-6 cyclized product, <I>N</I>-(2-cyanophenyl)-2-trifluoromethyl-3,3,3-trifluoropropionamide. The difference in reactivity between HFP and OFIB is discussed.
- 公益社団法人 日本化学会の論文
著者
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Nakai Takeshi
Department Of Applied Chemistry Tokyo Institute Of Technology
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Nakai Takeshi
Department of Chemical Engineering, Tokyo Institute of Technology
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Hassan Nabil
Department of Chemical Engineering, Tokyo Institute of Technology
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Ishikawa Nobuo
Department of Chemical Engineering, Tokyo Institute of Technology
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