Investigation of O-Sulfonylation-promoted Heterolytic NO Bond Cleavage of Amidoximes and Ketoximes

Tsung Han Hsieh, Pen Yuan Liao, Yu Ting Liu, Chien Hong Wang, Chia Chi Lin, Tun Cheng Chien

Research output: Contribution to journalArticle

Abstract

Two different reaction pathways were observed in the sulfonylation of N-phenylbenzamidoximes. The reaction with o-NsCl at a heating temperature gave N,N′-diphenylureas via Tiemann rearrangement, while the reaction with Ts2O at a lower temperature formed 2-phenylbenzimidazoles via intramolecular electrophilic aromatic substitution. When the amide nitrogen was replaced with carbon substituents, oxime derivatives of benzoins and benzils underwent Beckmann fragmentation reactions upon sulfonylation, whereas sulfonylation of 2-phenylacetophenone oxime afforded exclusively the Beckmann rearrangement adduct.

Original languageEnglish
Pages (from-to)325-330
Number of pages6
JournalJournal of the Chinese Chemical Society
Volume65
Issue number3
DOIs
Publication statusPublished - 2018 Mar

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Keywords

  • Beckmann fragmentation
  • Beckmann rearrangement
  • Electrophilic aromatic substitution
  • Tiemann rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

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