Photoaddition reaction of N-acetyldiphenylmethyleneamine with cyclic and acyclic olefins. An example of heavy atom effect in photoreaction.
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概要
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Irradiation of <I>N</I>-(diphenylmethylene)acetamide (<I>N</I>-acetyldiphenylmethyleneamine, <B>1</B>) in cyclopentene gave <I>N</I>-[1,1-diphenyl-1-(cyclopenta-2′-enyl)niethyl]acetaniide, the addition product of cyclopentene to the C=N bond of imine <B>1</B>, in 31% yield. The photoreaction of <B>1</B> was observed in other cyclic and acyclic olefins. The reactivity of the olefins decreases in the order; cyclopentene>cyclohexene>cyclooctene>2-pentene\simeq2-hexene. The photoreaction is promoted by the presence of the heavy atom solvent or the sensitizer. The mechanism of photoreaction is discussed in terms of the excited triplet state of the imine.
- 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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