A Kinetic Study of Cyclodehydration of β-Arylaminocroton-aldehyde Derivatives

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概要

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• Cyclodehydration of β-arylaminocrotonaldehydes (1) was studied kinetically in comparison with those of β-(p-toluidino)acrolein (2a) and 4-(p-toluidino)-3-penten-2-one (3a).The rate constants k_1 of cyclodehydration of 1 were not consistent with the Zucker-Hammett hypothesis, i.e., log k_1 was related linearly to -H_0,but the slopes were between 1.28 and 1.36.Bunnett-Olsen Plots for log k_1 were linear. Statistically corrected values of log k^0_r/K_<SH^+> were applied to Jaffe's four-parameter Hammett equation. The reaction constant for the site of the aromatic ring at which cyclodehydration takes place was evaluated to be -8.54,and that for the oxobutenyl-amino group was evaluated to be +0.72.The effect of substituents on the aromatic ring upon the reactivity is discussed.

• 社団法人日本薬学会の論文
• 1986-04-25

著者

• 尾能 満智子

  東邦大薬

• 尾能 満智子

  School Of Pharmaceutical Sciences Toho University

• 等々力 玲子

  School of Pharmaceutical Sciences, Toho University

• 田村 眞造

  School of Pharmaceutical Sciences, Toho University

• 田村 眞造

  School Of Pharmaceutical Sciences Toho University

• 田村 真造

  東邦大学 薬

• 等々力 玲子

  School Of Pharmaceutical Sciences Toho University

• Todoriki R

  Toho Univ. Chiba Jpn

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