Aromatic Nucleophilic Substitution. III. Meisenheimer Complexes in the Reactions of 1-(<I>N</I>,<I>N</I>-Dialkylamino)-2,4-dinitronaphthalenes with Sodium Methoxide

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概要

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• The intermediates in the reaction of 1-(<I>N</I>,<I>N</I>-dimethylamino)-2,4-dinitronaphthalene (<B>9</B>) with sodium methoxide have been studied in the mixtures of DMSO and CH<SUB>3</SUB>OH. The NMR spectra of the equimolar mixture of <B>9</B> and sodium methoxide indicate that <B>9</B> and a 1,1-disubstituted Meisenheimer complex coexist immediately after mixing, and that nearly all <B>9</B> changed into the Meisenheimer complex 15 min after mixing. The addition of 2 mol of sodium methoxide to 1 mol of <B>9</B> gave no 1,1,3,3-tetrasubstituted 2,4-dinitronaphthalene Meisenheimer complex. 1-Piperidino- or 1-(<I>N</I>-methyl-<I>N</I>-<I>n</I>-butylamino)-2,4-dinitronaphthalene reacted with sodium methoxide to give a similar Meisenheimer complex.

• 公益社団法人 日本化学会の論文

著者

• Shinozaki Katsuo

  Department of Synthetic Chemistry, Gunma University

関連論文

• Aromatic Nucleophilic Substitution. III. Meisenheimer Complexes in the Reactions of 1-(N,N-Dialkylamino)-2,4-dinitronaphthalenes with Sodium Methoxide

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