A New Rearrangement Reaction of Azoxybenzene with Arenesulfonyl Chloride

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概要

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• Azoxybenzene was found to react with arenesulfonyl chloride to afford <I>o</I>- or <I>p</I>-arenesulfonyloxyazobenzene. This new rearrangement reaction is found in various substituted azoxybenzenes and arenesulfonyl chlorides. By the use of the <SUP>18</SUP>O tracer technique, the <I>ortho</I> rearrangement was found to proceed <I>via</I> an intramolecular path, while the rearrangement to the <I>para</I> position was intermolecular. The yields of the rearranged products were determined by the isotopic dilution technique, while the migratory aptitude was also determined by the use of azoxybenzene-1-<SUP>14</SUP>C. It was found that the ratio of the sulfonyloxy migration to the phenyl ring attached to the azoxy side to that of the azo side is 1 to 2 for the <I>ortho</I> rearrangement. On the bases of these observations, the mechanism of this new rearrangement reaction is discussed.

• 公益社団法人 日本化学会の論文

著者

• Maeda Tetsuya

  Department Of Applied Chemistry And Chemical Engineering Yamaguchi University

• Oae Shigeru

  Deparment of Applied Chemistry Faculty of Engineering Osaka City University

• Maeda Tetsuya

  Department of Applied Chemistry, Osaka City University

• Kozuka Seizi

  Department of Applied Chemistry, Osaka City University

• Nakai Mamoru

  Department of Applied Chemistry, Osaka City University

• Nakai Mamoru

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

• Kozuka Seizi

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

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