Synthesis and characterization of 2-methoxy-2H-azepines: the first isolation of 2-azanorcaradiene, the valence isomer of 3H-azepine

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Kyosuke Satake, Yuko Tawada, Hideki Okamoto and Masaru Kimura


Abstract

The selective formation of 2-methoxy-2H-azepine from 3H-azepines, via a likely azatropylium cation, is reported; the first isolation of 2-azanorcaradiene, which is considered to be the valence isomer of 3H-azepine, is also described.


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