Cationic Arylation. II. Phenylation of Substituted Benzenes with Phenylazo-<I>p</I>-tolylsulfone in Acidic Solutions
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概要
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The acid-catalyzed decomposition of phenylazo-<I>p</I>-tolylsulfone was studied in PhX, PhX-CH<SUB>3</SUB>CN and PhX-DMSO (X=OCH<SUB>3</SUB>, C<SUB>2</SUB>H<SUB>5</SUB>, CH<SUB>3</SUB>, Cl, CO<SUB>2</SUB>CH<SUB>3</SUB>, NO<SUB>2</SUB>). The decomposition was of first order but was faster with greater concentration of trifluoroacetic acid. The orientation and the partial rate factors for the phenylation of substituted benzenes were quite different from those for the radical phenylation but quite similar to those for the phenylation with phenyl cation generated from PhN<SUB>2</SUB><SUP>+</SUP>BF<SUB>4</SUB><SUP>−</SUP>. Experiments with deuterated compounds indicated that the abstraction of proton from the phenylated complex was not rate-determining. A mechanism involving phenyl cation was proposed for the acid-catalyzed decomposition of azosulfone.
- 公益社団法人 日本化学会の論文
著者
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Minato Hiroshi
Department Of Electrical Engineering And Computer Science Tufts University
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KOBAYASHI Michio
Department of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin Un
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Kobori Nobumasa
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University
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