1971 Volume 44 Issue 10 Pages 2776-2779
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
and that on carbonyl-carbon is
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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