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Communication | Regular issue | Vol 60, No. 10, 2003, pp.2211-2215
Published online, 18th August, 2003
DOI: 10.3987/COM-03-9851
■ Plausible Mechanism for the Formation of 2-Methoxy-2H-azepine Derivatives from 3H-Azepines Using Bromine and NBS

Kyosuke Satake,* Christopher Cordonier, Yasuhiro Kubota, Yuexian Jin, and Masaru Kimura

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

Formation of 2-bromo-4-t-butyl-7-methoxy-2H-azepine and 4-t-butyl-7-methoxy-2-succinimidyl-2H-azepine by the respective reactions of 5-t-butyl-2-methoxy-3H-azepine with bromine and NBS suggests a plausible mechanism for the conversion of 3H-azepine to 2H-azepine as 1,4-addition of an electrophile and a consequent 1,2-dehydrobromination. Different from the case of cycloheptatriene, reaction of 3H-azepine with bromine did not give any delocalized ionic species.