Abstract / Description of output
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 language | English |
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Pages (from-to) | 2821-2827 |
Journal | European Journal of Organic Chemistry |
Volume | 2016 |
Issue number | 16 |
DOIs | |
Publication status | Published - 23 May 2016 |
Keywords / Materials (for Non-textual outputs)
- ureas
- rearrangement
- elimation
- reaction mechanisms