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Short Paper | Regular issue | Vol 102, No. 3, 2021, pp.534-545
Published online, 29th January, 2021
DOI: 10.3987/COM-20-14401
Stepwise Reactions between Cyclic 1,4-Diazadienes and Ketenes: Characteristics and Mechanism

Kazuhide Nakahara,* Koki Yamaguchi, and Hisao Kansui

*Department of Integrative Pharmaceutical Sciences, Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan


The reaction of unsymmetrical monophenyl cyclic 1,4-diazadienes with ketene derivatives yields new structures via 1,5-sigmatropic reactions. These structures were determined and confirmed by single-crystal X-ray analysis. The reaction mechanism was investigated by density functional theory calculations. The result of the calculation indicated whether the reaction was a cyclization reaction or a 1,5-shift rearrangement based on the stability of the intermediate conformation.