Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Hofmann Rearrangement. IV. Kinetic Isotope Effect of N-Chlorobenzamide
Tsuneo ImamotoSeung-Geon KimYuho TsunoYasuhide Yukawa
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1971 Volume 44 Issue 10 Pages 2776-2779

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Abstract

Kinetic isotope effects in the Hofmann rearrangement of phenyl-1-14C and carbonyl-14C labeled N-chlorobenzamides were measured in a sodium hydroxide solution at 15°C. The observed isotope effect on the phenyl-1-carbon is
k12k14=1.0456±0.0012
and that on carbonyl-carbon is
k12k14=1.0447±0.0006
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 r-value of the linear aromatic substituent-reactivity relationship in related 1,2-rearrangements.

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