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A versatile new synthesis of 1H-azepines

✍ Scribed by Leo A. Paquette; Donald E. Kuhla

Publisher: Elsevier Science
Year: 1967
Tongue: French
Weight: 177 KB
Volume: 8
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)89546-0

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✦ Synopsis

Derivatives of lH-azepine (j_), the 8n electron azalog of the unstable cycloheptatrienide anion, were first reported in 1g63.4 These interesting heterocycles are produced in good to excellent yield by the reaction of benzene with nitrenes generated in situ by thermolysis or photolysis of appropriate azides.5 When the reaction is extended to such as toluene, bromobenzene, and anisole, however, there results a azepines which, in general, defy preparative scale vpc separati0n.e stances, various studies of the ground-and excited-state properties tives of1 have not heretofore been capable of realization. As part 'This subject will form the content of future papers.

The parent compound (&, R = COOCHe) has also been prepared by this reaction sequence in good overall yield.

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