Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization

Christopher E.J. Cordonier; Kyosuke Satake; Hideki Okamoto; Masaru Kimura

doi:10.1002/ejoc.200600257

Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization

Christopher E.J. Cordonier, Kyosuke Satake, Hideki Okamoto, Masaru Kimura

Research output: Contribution to journal › Article

10 Citations (Scopus)

Abstract

2-Aryl-2H-, 3-aryl-3H-, and 4-aryl-4H-azepine were formed by the novel, electrophilic, π_LUMO-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	https://doi.org/10.1002/ejoc.200600257
Publication status	Published - Aug 25 2006

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Keywords

1,5-Hydrogen shift
4H-Azepine
Azepinium
Density functional calculations
Heterocycles

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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

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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.",

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AU - Okamoto, Hideki

AU - Kimura, Masaru

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AB - 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.

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10.1002/ejoc.200600257