Abstract
IN a recent communication under the above title, Heller, Hughes and Ingold1 have discussed an anionotropic mechanism for the acid-catalysed rearrangement of phenylhydroxylamine to p-amino-phenol, the essential feature of which is the migration of the hydroxyl group with its full electron octet and which involves the following steps : (i) conversion of the hydroxylamine into its conjugate acid, (ii) inter-molecular migration of the hydroxyl group in the form of a water molecule, (iii) prototropic isomerization of the resulting iminoquinol and loss of a proton to give the aminophenol. This mechanism is identical in substance with that which I have previously put forward and expressed in the following formulæ2: .
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References
Nature, 168, 909 (1951).
Quart. Rev. Chem. Soc., 4, 423 (1950).
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BRAUDE, E. A New View of the Arylhydroxylamine Rearrangement. Nature 169, 80 (1952). https://doi.org/10.1038/169080a0
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DOI: https://doi.org/10.1038/169080a0
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