Organic letters

Electrophilic Behavior of the π Delocalized Azepinium Ion: Friedel-Crafts Reactions with Benzenes and Five-Membered Aromatic Heterocycles

Y Kubota, K Satake, H Okamoto, M Kimura

Index: Kubota, Yasuhiro; Satake, Kyosuke; Ikui, Ryusuke; Okamoto, Hideki; Kimura, Masaru Bulletin of the Chemical Society of Japan, 2003 , vol. 76, # 4 p. 805 - 811

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Citation Number: 12

Abstract

Although the reactivity of tropylium ion with aromatic substrates is low, the reaction of azepinium ion with aromatic substrates such as benzene, phenol, furan, and thiophene resulted in the formation of 2-aryl-2 H-azepine as a major product. An exceptional result in the formation of ring-contracted product was observed in the reaction with pyrrole.