O-Phenylisourea Synthesis and Deprotonation: Carbodiimide Elimination Precludes the Reported Chapman Rearrangement

Joseph A. Tate, George Hodges, Guy C. Lloyd-jones

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)2821-2827
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number16
DOIs
Publication statusPublished - 23 May 2016

Keywords

  • ureas
  • rearrangement
  • elimation
  • reaction mechanisms

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