Photoreduction and Photoaddition of <I>N</I>-Acetyldiphenylmethyleneamine in Alkylbenzenes
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概要
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Irradiation of <I>N</I>-acetyldiphenylmethyleneamine (II) in toluene solution gave <I>N</I>-(1,1,2-triphenylethyl)acetamide and <I>N</I>-(1,1-diphenylmethyl)acetamide in 11% and 4.4% yields, respectively. The former is an addition product of toluene to the C=N bond of imine II, and the latter a hydrogenation product of II. The same kind of addition and hydrogenation products as those in toluene were obtained on irradiation of imine II in ethylbenzene, cumene, <I>o</I>-, <I>m</I>-, and <I>p</I>-xylene, mesitylene, <I>p</I>-methoxytoluene, and <I>p</I>-cyanotoluene, respectively. Two kinds of competitive reaction processes are proposed from the results of the substituent effects for the phenyl ring of toluene, the effect of the additives such as sensitizers and quenchers, and the dependence of the photoreaction yields on the concentration of the additive. The photoreaction proceeds not only by the "chemical sensitization" mechanism derived from the ketyl radical of benzophenone, a hydrolyzed product of II, but also by the mechanism through the excited state of II itself.
- 公益社団法人 日本化学会の論文
著者
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Toshima Naoki
Department Of Applied Chemistry
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Hirai Hidefumi
Department Of Industrial Chemistry Faculty Of Engineering Science University Of Tokyo
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Asao Shuichiro
Department of Industrial Chemistry, Faculty of Engineering, The University of Tokyo
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