87944-19-2

Upstream product

• 88-89-1 2,4,6-Trinitrophenol 
• 693-13-0 diisopropyl-carbodiimide 
• 108-95-2 phenol 

Downstream Products

• 60683-30-9 ethyl N,N′-diisopropylcarbamimidate 
• 88-89-1 2,4,6-Trinitrophenol 
• 108-95-2 phenol 
• 87931-27-9 NN'-di-isopropyl-N-phenylurea 

Relevant academic research and scientific papers

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

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.

Degradation of O-Arylisoureas in Alkali: A Low-temperature Chapman-type Rearrangement

NN'-Di-isopropyl-O-arylisoureas are demonstrated to rearrange intramolecularly to the corresponding NN'-di-isopropyl-N'-arylurea in alkaline solution.The large negative Broensted-type βL value (-2.3) for the reaction measured against the pK of the corresponding phenol and a modest entropy of activation are consistent with a 1,3-aryl migration.The high efficiency of the migration compared with that of the Chapman rearrangement of O-aryl imidoethers is attributed to the greater internal nucleophilicity of the imino nitrogen, which in the present case bears a negative charge.