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 language | English |
|---|---|
| Pages (from-to) | 325-330 |
| Number of pages | 6 |
| Journal | Journal of the Chinese Chemical Society |
| Volume | 65 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2018 Mar |
Keywords
- Beckmann fragmentation
- Beckmann rearrangement
- Electrophilic aromatic substitution
- Tiemann rearrangement
ASJC Scopus subject areas
- Chemistry(all)
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Hsieh, T. H., Liao, P. Y., Liu, Y. T., Wang, C. H., Lin, C. C., & Chien, T. C. (2018). Investigation of O-Sulfonylation-promoted Heterolytic NO Bond Cleavage of Amidoximes and Ketoximes. Journal of the Chinese Chemical Society, 65(3), 325-330. https://doi.org/10.1002/jccs.201700104