Re-examination of the Anodic Dimerization of Enamines, 2-Cyano-2-phenylvinylamines, Using the Austin Model 1 Method

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概要

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• Dimerization of cation redicals derived from 2-cyano-2-phenylvinylamines (1) to produce diphenylmethane derivatives (Ph-CH(CN)-C_6H_4-C(CN)=CH-NR^2R^3,2) was re-examined by the AM1 (Austin model 1) method.However, dimerization of cation radicals derived from 1 was forbidden by calculation of the total energies of the dimers. An alternative reaction mechanism for the formation of 2 was proposed. Hydrolysis of cation radical (A) derived from N, N-dimethyl-2-cyano-2-phenylvinylamine (1a) gives a cyanophenylmethyl radical (F), which attacks at 1a to give a redical (G). Following anodic oxidation of G, deprotonation gives phenyl-[4-(1-cyano-2-dimethylaminovinyl)phenyl]acetonitrile (2a) as the final product.

• 公益社団法人日本薬学会の論文
• 1999-07-15

著者

• YAMAOKA Yumiko

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• Yamaoka Y

  Kobe‐gakuin Univ. Kobe Jpn

• Yamaoka Yumiko

  Faculty Of Pharmaceutical Sciences And High-technology Research Center Kobe-gakuin University

• OSAWA Eriko

  Faculty of Pharmaceutical Sciences and High-Technology Research Center, Kobe-Gakuin University

• MICHIDA Takashi

  Faculty of Pharmaceutical Sciences Kobe-Gakuin University

• SAITO Tsuneaki

  Faculty of Pharmaceutical Sciences, Kobe-Gakuin University

• Saito Tsuneaki

  Faculty Of Pharmaceutical Sciences Kobe-gakuin University

• Osawa E

  Kobe‐gakuin Univ. Hyogo Jpn

• Osawa Eriko

  Faculty Of Pharmaceutical Sciences And High-technology Research Center Kobe-gakuin University

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