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- Title
Investigation of O‐Sulfonylation‐promoted Heterolytic NO Bond Cleavage of Amidoximes and Ketoximes.
- Authors
Hsieh, Tsung‐Han; Liao, Pen‐Yuan; Liu, Yu‐Ting; Wang, Chien‐Hong; Lin, Chia‐Chi; Chien, Tun‐Cheng
- 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.
- Subjects
OXIME derivatives; SCISSION (Chemistry); ELECTROPHILIC substitution reactions; BECKMANN rearrangement; SUBSTITUENTS (Chemistry)
- Publication
Journal of the Chinese Chemical Society, 2018, Vol 65, Issue 3, p325
- ISSN
0009-4536
- Publication type
Article
- DOI
10.1002/jccs.201700104