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.
- 1,5-Hydrogen shift
- Density functional calculations
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry