Aromatic nucleophilic substitution. VI. 1H nuclear magnetic resonance evidence for the rearrangement of 1,3- to 1,1-anionic .SIGMA. complex in the reactions of 1-dialkylamino-2,4-dinitronaphthalenes with potassium alkoxides.
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概要
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By use of NMR spectroscopy the rearrangement of 1,3- to 1,1-anionic σ complex (Meisenheimer complex) in the reactions of 1-dialkylamino-2,4-dinitronaphthalenes (dimethylamino-, diethylamino-, and <I>N</I>-methyl-<I>N</I>-butylamino, piperidyl) with potassium alkoxides in DMSO has been studied. The alkoxides used are potassium methoxide, ethoxide, isopropoxide, and <I>t</I>-butoxide. In the reactions of 1-dialkylamino-2,4-dinitronaphthalenes with the alkoxides the rearrangement could be spectrometrically analyzed. However, in the reaction of 1-dimethylamino-2,4-dinitro naphthalene with potassium <I>t</I>-butoxide the rearrangement was too fast to be clearly analyzed.
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著者
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Ando Yumiko
Synthetic Chemistry Department, Gunma University
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Sekiguchi Shizen
Synthetic Chemistry Department, Gunma University
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Fujisawa Shigeru
Synthetic Chemistry Department, Gunma University