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 |
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Keywords
- 1,5-Hydrogen shift
- 4H-Azepine
- Azepinium
- Density functional calculations
- Heterocycles
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization. / Cordonier, Christopher E J; Satake, Kyosuke; Okamoto, Hideki; Kimura, Masaru.
In: European Journal of Organic Chemistry, No. 17, 25.08.2006, p. 3803-3807.Research output: Contribution to journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=33748554152&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33748554152&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200600257
DO - 10.1002/ejoc.200600257
M3 - Article
AN - SCOPUS:33748554152
SP - 3803
EP - 3807
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 17
ER -