Homolytic aromatic substitution by iminyl radicals. Photolysis of aromatic ketone O-acyloximes in aromatic solvents.

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概要

• 論文の詳細を見る

• Irradiation of benzophenone <I>O</I>-acetyloxime, <I>O</I>-phenylacetyloxime, <I>O</I>-benzoyloxime, and <I>O</I>-(<I>p</I>-chlorobenzoyl)oxime in benzene, toluene, chlorobenzene, or <I>o</I>-xylene effected aromatic substitution on the solvent molecules by diphenylmethaniminyl radicals to give <I>N</I>-diphenylmethylenearylamines only when benzoxyl or <I>p</I>-chlorobenzoxyl radicals were generated concurrently. A mechanism involving a participation of the sufficiently long-lived acyloxyl radicals is proposed for the iminylation reaction on the basis of the reactivity patterns in this substitution reaction. <I>o</I>-Phenylbenzophenone <I>O</I>-benzoyloxime was also photolyzed in benzene to give 9-phenylphenanthridine, the intramolecular cyclization product of 2-biphenylylphenylmethaniminyl radicals.

• 公益社団法人 日本化学会の論文

著者

• NISHIMURA Toshihiro

  Department of Applied Chemistry, Faculty of Science, Science University of Tokyo

• Sakuragi Hirochika

  Department Of Chemistry University Of Tsukuba

• Tokumaru Katsumi

  Institute Of Chemistry University Of Tsukuba

• Yoshida Masayuki

  Department Of Applied Genetics Medical Research Institute Tokyo Medical And Dental University

• Sakuragi Hirochika

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Nishimura Toshihiro

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Inamoto Naoki

  Department of Chemistry and Research Centre for Spectrochemistry, Faculty of Science, The University of Tokyo

• Ishikawa Shun-ichi

  Department of Chemistry, Faculty of Science, The University of Tokyo

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