A New View of the Arylhydroxylamine Rearrangement

Abstract

IT is a commonplace that those acid-catalysed aromatic rearrangements, which conform to the general pattern, notwithstanding that they are formally so similar, do not all proceed by the same mechanism: some involve intermolecular processes and some intramolecular. But they are usually all held to have at least this in common, namely, that X migrates as an electrophilic fragment: whatever adventures it may go through while in transit, it separates from nitrogen without the electrons by which it was bound thereto, and it unites with aromatic carbon by means of electrons which the latter has to supply. Such rearrangements may be called ‘electrophilic rearrangements’.

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References

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    Dewar, ‘Electronic Theory of Organic Reactions’, 225 (Oxford Univ. Press, 1949).

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HELLER, H., HUGHES, E. & INGOLD, C. A New View of the Arylhydroxylamine Rearrangement. Nature 168, 909–910 (1951). https://doi.org/10.1038/168909a0

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