Photoinduced intramolecular aromatic nucleophilic substitution (the photo-Smiles rearrangement) in amino ethers.
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概要
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Intramolecular rearrangement was induced by light as well as base in a homologous series of 1-(<I>p</I>-nitrophenoxy)-ω-anilinoalkanes, <I>p</I>-O<SUB>2</SUB>NC<SUB>6</SUB>H<SUB>4</SUB>O(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>NHPh(<I>n</I>=2–5), yielding <I>N</I>-(<I>p</I>-nitrophenyl)-ω-anilino-1-alkanols, <I>p</I>-O<SUB>2</SUB>NC<SUB>6</SUB>H<SUB>4</SUB>N(Ph)(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>OH. The reaction rate in acetonitrile showed abnormal order, <I>n</I>=4>5>3>2, which was reversed by the addition of triethylamine. The mechanism of this photorearrangement through a radical ion pair and a spiro type Meisenheimer complex was proposed. The anomaly in the reaction rate order was discussed on the basis of this mechanism.
- 公益社団法人 日本化学会の論文
著者
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Kobayashi Keiji
Department Of Chemistry College Of Arts And Sciences The University Of Tokyo
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Mutai Kiyoshi
Department Of Chemistry Graduate School Of Arts And Sciences The University Of Tokyo
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Kobayashi Keiji
Department of Chemistry, College of General Education, The University of
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Mutai Kiyoshi
Department of Chemistry, College of General Education, The University of
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