Abstract
2-Aryl-2H-, 3-aryl-3H-, and 4-aryl-4H-azepine were formed by the novel, electrophilic, πLUMO-controlled reaction of the 2-methoxyazepinium ion, generated in situ by the reaction of TiCl4 with 2,7-dialkoxy-2H-azepine and an aryl compound, for which the kinetic parameters of the sigmatropic hydrogen rearrangement of the 4H-azepine was measured. The substitution and hydrogen shift of the azepinium ion were analyzed with DFT studies.
| Original language | English |
|---|---|
| Pages (from-to) | 3803-3807 |
| Number of pages | 5 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - Aug 25 2006 |
Keywords
- 1,5-Hydrogen shift
- 4H-Azepine
- Azepinium
- Density functional calculations
- Heterocycles
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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Cite this
Cordonier, C. E. J., Satake, K., Okamoto, H., & Kimura, M. (2006). Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization. European Journal of Organic Chemistry, (17), 3803-3807. https://doi.org/10.1002/ejoc.200600257