Aryliminodimagnesium reagents. XIV. Reactions with nitrobenzenes having electronegative ortho-substituents. Effects of reaction conditions on condensation, replacement, and substitution.

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概要

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• In reactions of ArN(MgBr)<SUB>2</SUB> with <I>o</I>-MeO- and <I>o</I>-halo-substituted nitrobenzenes, types and yields of products were different from those in its reactions with <I>m</I>- and <I>p</I>-substituted substrates. Condensation (leading to unsymmetrical azoxy- and azobenzenes), <I>o</I>-substituent replacement, and nuclear substitution took place. Relative yields of products were greatly affected by substituents and reaction conditions. <I>o</I>-MeO and <I>o</I>-F favor replacement, while <I>o</I>-Cl, <I>o</I>-Br, and <I>o</I>-I favor substitution. Replacement and/or substitution predominate when small molar excess of reagent and low concentration are used, while condensation predominates when large molar excess of reagent and high concentration are used, which phenomenon is mechanistically discussed.

• 公益社団法人 日本化学会の論文

著者

• Imamura Kaori

  Department Of Plant Science School Of Agriculture Tokai University

• Taniguchi Naoki

  Department of Chemistry, Faculty of Science and Engineering, Saga University

• Okubo Masao

  Department of Chemistry, Faculty of Science and Engineering, Saga University

• Inatomi Yoshito

  Department of Chemistry, Faculty of Science and Engineering, Saga University

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