Formation of 4H??Azepine by the Electrophilic Reaction of a 2??Methoxyazepinium Ion and Analysis of the Sigmatropic Isomerization

CEJ Cordonier, K Satake, H Okamoto…

Index: Cordonier, Christopher E. J.; Satake, Kyosuke; Okamoto, Hideki; Kimura, Masaru European Journal of Organic Chemistry, 2006 , # 17 p. 3803 - 3807

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Citation Number: 8

Abstract

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 TiCl 4 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 ...