The Hofmann Rearrangement. IV. Kinetic Isotope Effect of <I>N</I>-Chlorobenzamide
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概要
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Kinetic isotope effects in the Hofmann rearrangement of phenyl-1-<SUP>14</SUP>C and carbonyl-<SUP>14</SUP>C labeled <I>N</I>-chlorobenzamides were measured in a sodium hydroxide solution at 15°C. The observed isotope effect on the phenyl-1-carbon is<BR><I>k</I><SUB>12</SUB>⁄<I>k</I><SUB>14</SUB>=1.0456±0.0012<BR>and that on carbonyl-carbon is<BR><I>k</I><SUB>12</SUB>⁄<I>k</I><SUB>14</SUB>=1.0447±0.0006<BR>These results strongly support a concerted mechanism for this rearrangement. Attempts have been made to correlate the isotope effect on phenyl-1-carbon to the <I>r</I>-value of the linear aromatic substituent-reactivity relationship in related 1,2-rearrangements.
- 公益社団法人 日本化学会の論文
著者
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TSUNO Yuho
The Institute for Fundamental Research of Organic Chemistry, Kyushu University
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Kim Seung-Geon
The Institute of Scientific and Industrial Research, Osaka University
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Imamoto Tsuneo
The Institute of Scientific and Industrial Research, Osaka University
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Yukawa Yasuhide
The Institute of Scientific and Industrial Research, Osaka University
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