Journal of the Chemical Society. Perkin transactions II p. 1369 - 1372 (1983)
Update date:2022-07-29
Topics:
Suttle, Nicola A.
Williams, Andrew
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.
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