Photoinduced nucleophilic addition of ammonia and alkylamines to aryl-substituted alkenes in the presence of p-dicyanobenzene.
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概要
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The photoamination of 1,1-diphenylpropene (<B>1a</B>) with ammonia and some primary alkylamines in the presence of <I>p</I>-dicyanobenzene gave the corresponding <I>N</I>-substituted 2-amino-1,1-diphenylpropane (<B>2a–e</B>) along with the formation of 3-methyl-4,4-diphenylbutanenitrile (<B>3a</B>), 1,1-diphenylpropane (<B>4a</B>), 3,3-diphenylpropene (<B>5</B>), and diphenylmethane (<B>6</B>). In the case of 1,1-diphenylethene (<B>1b</B>), <I>N</I>-substituted 1-amino-2,2-diphenylethane (<B>2f–h</B>), 4,4-diphenylbutanenitrile (<B>3b</B>), and 1,1-diphenylethane (<B>4b</B>) were produced. In photoamination with <I>t</I>-butylamine in acetonitrile, <B>3a</B> and <B>3b</B> were mainly formed as a consequence of the incorporation of acetonitrile to <B>1a</B> and <B>1b</B>. The photoamination of 1-phenyl-3,4-dihydronaphthalene (<B>1c</B>) with isopropylamine or <I>t</I>-butylamine gave <I>cis</I>- and <I>trans</I>-<I>N</I>-substituted 1-phenyl-2-amino-1,2,3,4-tetrahydronaphthalenes (<B>15</B> and <B>16</B>) in a ratio of ca. 8:2. The mechanism of photoamination is discussed in terms of a photochemical electron transfer of <B>1</B> to <I>p</I>-dicyanobenzene followed by a nucleophilic addition of the amine to the cation radical of <B>1</B>.
- 公益社団法人 日本化学会の論文
著者
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Shima Kensuke
Department Of Applied Chemistry Faculty Of Engineering Miyazaki University
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Shiomori Koichiro
Department Of Applied Chemistry Miyazaki University
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YAMASHITA Toshiaki
Department of Chemical Science and Engineering, Miyakonojo National College of Technology
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YASUDA Masahide
Depariment of Hygienic Chemistry, Osaka College of Pharmacy
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Shiomori Koichiro
Department of Industrial Chemistry, Faculty of Engineering, Miyazaki University
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Yamashita Toshiaki
Department of Industrial Chemistry, Miyakonojo National College of Technology
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