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[Phenoxenium ions: generations and reactions]

Y Endo1, K Shudo

  • 1Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.

Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan
|August 1, 1994
PubMed
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This study reveals that acid-catalyzed reactions of N-acyl- and N-sulfonylhydroxylamines with benzene yield C-C products like hydroxybiphenyls. A mechanism involving a phenoxenium ion intermediate explains these and other related reactions, including rearrangements.

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Context:

  • Investigating the reactivity of N-acyl- and N-sulfonylhydroxylamines.
  • Exploring the thermolysis of N-aryloxypyridinium salts.

Purpose:

  • To elucidate the mechanism of acid-catalyzed reactions with benzene.
  • To identify key intermediates and reaction pathways.

Summary:

  • Acid catalysis of N-acyl- and N-sulfonylhydroxylamines with benzene produces 2- and 4-hydroxybiphenyls (C-C products).
  • A phenoxenium ion intermediate, with charge delocalized to ortho and para carbons, is proposed.
  • Diphenyl ethers (C-O products) form via SN2-like reactions when N-O bond heterolysis is slow.
  • Phenoxenium ions also mediate the rearrangement of O-arylhydroxylamines to 2-aminophenols.

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Impact:

  • Provides mechanistic insight into C-C and C-O bond formation reactions.
  • Expands understanding of phenoxenium ion chemistry and reactivity.
  • Offers a basis for designing new synthetic routes involving hydroxylamine derivatives.