Aromatic nucleophilic substitution. XIII. Confirmation of the anionic .SIGMA. complexes in the reactions of 2,4-dinitro- and 2,4,5-trinitro-1-(1-piperidyl)naphthalenes with piperidine in dimethyl sulfoxide.
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概要
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In the reactions of 2,4-dinitro- and 2,4,5-trinitro-1-(1-piperidyl)naphthalenes with piperidine in dimethyl sulfoxide, the 1,1-disubstituted anionic σ complex was confirmed to exist with visible absorption and NMR spectra. Especially in the latter case the 1,3-disubstituted anionic σ complex was formed, the cause of formation of which was ascribed to the deactivating effect of 1-piperidyl group on C<SUB>1</SUB>-position of a napthtalene ring and the steric effect of 1-piperidyl group on the nucleophilic attack of piperidine on C<SUB>1</SUB>-position. These factors make the 1,1-disubstituted anionic a complex unstable.
- 公益社団法人 日本化学会の論文
著者
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Ando Yumiko
Department Of Radiology Nishibeppu National Hospital
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Sekiguchi Shizen
Department of Chemistry, Faculty of Engineering, Gunma University
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Matsui Kohji
Department of Chemistry, Faculty of Engineering, Gunma University
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Tomoto Noboru
Faculty of Engineering, Miyazaki University
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Ando Yumiko
Department of Synthetic Chemistry, Gunma University
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Hikage Reiko
Department of Synthetic Chemistry, Gunma University
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Obana Kenmi
Department of Synthetic Chemistry, Gunma University
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