Dearomatization of a benzene ring using intramolecular 1,3-dipolar cycloaddition of nitrile <I>N</I>-oxide

DOI

Bibliographic Information

Other Title
  • ニトリルオキシドの分子内1,3-双極子環化付加による脱芳香族化反応

Description

This paper describes a dearomatization of a benzene ring of 2-phenoxybenzonitrile N-oxide derivatives by intramolecular 1,3-dipolar cycloaddition of nitrile N-oxide. It is known that treatment of polycyclic aromatic hydrocarbons such as pyrene, anthracene or C60 with nitrile N-oxide afford 1,3-dipolar cycloadducts along with dearomatization. However, 1,3-dipolar addition of nitrile N-oxide to monocyclic aromatics is difficult due to the low reactivity. For such issues, we focused on the intramolecular 1,3-dipolar reaction of nitrile N-oxide with monocyclic aromatics. Dihydroxybenzoisoxazole derivative was obtained in good yield by refluxing 2-(4-methylphenyl)-6-methoxybenzonitrile N-oxide, generated from the corresponding oxime with N-chlorosuccinic imide (NCS) and Et3N in CHCl<SUB>3<SUB>. The single crystal X-ray diffraction revealed that the 1,3-dipolar cycloaddition reaction provided cis-adduct as a single isomer. The scope and limitation of the reaction would be discussed from the viewpoint of electron demand and steric effect on the benzene rings.

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Details 詳細情報について

  • CRID
    1390001205555907584
  • NII Article ID
    130004729152
  • DOI
    10.11494/kisoyuki.2010.0.2p14.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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