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
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U2 - 10.1002/ejoc.200600257
DO - 10.1002/ejoc.200600257
M3 - Article
AN - SCOPUS:33748554152
SN - 0075-4617
SP - 3803
EP - 3807
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
IS - 17
ER -