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Communication | Regular issue | Vol 12, No. 5, 1979, pp.657-660
Published online, 1st January, 1970
DOI: 10.3987/R-1979-05-0657
N-Substituent Effect of 4-Amino-3-penten-2-one in the Reaction with Phenylhydrazine

Choji Kashima,* Shunichi Shirai, and Yasuhiro Yamamoto

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


The reaction rates of p-substituted 4-amino-3-penten-2-ones with phenylhydrazine were not comparable to the value of superdelocalizability for a nucleophile, but for an electrophile. From this result, the rate determing step was speculated to be the protonation on a substrate. The electron-donating group on nitrogen atom accelerated the reaction of 3-amino-2-en-1-ones with nucleophiles, especially in the presence of acid.