The Hofmann Rearrangement. III. Kinetic Substituent Effects of 4- and 5-Substituted 2-Chloro-<I>N</I>-chlorobenzamides

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概要

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• The kinetic measurements of the Hofmann rearrangement of 2,4-, 2,5- 2,6-, and 3,5-disubstituted <I>N</I>-chlorobenzamides were carried out. The rate constants of 4- and 5-substituted 2-chloro-<I>N</I>-chlorobenzamides were applicable to the LArSR relationship:<BR>log<I>k</I>⁄<I>k</I><SUB>0</SUB>=−2.21(σ<SUP>0</SUP>+0.69<I>Δ</I>\barσ<SUB>R</SUB><SUP>+</SUP>)+0.003<BR>indicating that the reactivity of the 2-chloro series was subjected to a larger additional conjugation effect than that of the 2-unsubstituted series. The detailed discussion of the reaction mechanism on the basis of these results supported strongly the concerted mechanism.

• 公益社団法人 日本化学会の論文

著者

• TSUNO Yuho

  The Institute for Fundamental Research of Organic Chemistry, Kyushu University

• Imamoto Tsuneo

  The Institute of Scientific and Industrial Research, Osaka University

• Yukawa Yasuhide

  The Institute of Scientific and Industrial Research, Osaka University

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