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*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

摘要

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.

原文英語
頁(從 - 到)325-330
頁數6
期刊Journal of the Chinese Chemical Society
65
發行號3
DOIs
出版狀態已發佈 - 2018 三月

ASJC Scopus subject areas

  • 化學 (全部)

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