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Communication | Regular issue | Vol 32, No. 1, 1991, pp.1-6
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5495
1,3-Dipolar Cycloadditions of N,α-Diphenylnitrone to the 4,5-Positions of 1H-Azepine and 1H-1,2-Diazepine Derivatives: Formation of endo- and exo-Type Cycloadducts and Computer-assisted Line Shape Simulation of the Nmr spectra of the Adducts

Katsuhiro Saito,* Akihiro Yoshino, and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Reaction of 1-carbomethoxy-1H-azepine with N,α-diphenylnitrone afforded two stereochemical isomers in almost the same ratio. The analysis of the nmr spectra of the cycloadducts were confirmed by good coincidence of the spectra to those obtained by computer assisted line shape simulation. The analogous result was obtained in the reaction using 1-carboethoxy-1H-1,2-diazepine. The reaction is considered to proceed through concerted [4+2]-type 1,3-dipolar cycloadditions of the nitrone to 4,5-positions of the azepine or diazepine to give endo- and exo-type adducts because of the absence of stabilization effects by secondary orbital interactions in the transition states.