Abstract
The kinetics of the addition of phenol to diisopropylcarbodiimide, and reaction of the resulting N,N′‐diisopropyl‐O‐phenylisourea with hydroxide, are reported. The isourea is generated by a slow overall termolecular equilibrium process, inhibited by isourea–phenol salt generation. In contrast to an earlier report, reaction of the isourea with hydroxide does not induce a synthetically useful 1,3‐O–N (Chapman) rearrangement. Instead, deprotonation results in solvolysis by carbodiimide elimination.
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