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 › peer-review

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

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

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.",

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

author = "Cordonier, {Christopher E.J.} and Kyosuke Satake and Hideki Okamoto and Masaru Kimura",

year = "2006",

month = aug,

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doi = "10.1002/ejoc.200600257",

language = "English",

pages = "3803--3807",

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T1 - Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization

AU - Cordonier, Christopher E.J.

AU - Satake, Kyosuke

AU - Okamoto, Hideki

AU - Kimura, Masaru

PY - 2006/8/25

Y1 - 2006/8/25

N2 - 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.

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.

KW - 1,5-Hydrogen shift

KW - 4H-Azepine

KW - Azepinium

KW - Density functional calculations

KW - Heterocycles

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