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Migration of Acyl Groups from Side-chain Nitrogen to Nuclear Carbon

Abstract

THE Claisen and Fries rearrangements embody the migrations of alkyl and acyl groups respectively, from oxygen of the side-chain to carbon of the aromatic nucleus. Where nitrogen occupies the position of oxygen in the foregoing side-chain, the migration of alkyl to the nucleus is again a familiar rearrangement (Hofmann-Martius), but the movement of acyl groups from side-chain nitrogen (parallel to the Fries reaction in the phenol system) is not so well known.

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References

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DIPPY, J., WOOD, J. Migration of Acyl Groups from Side-chain Nitrogen to Nuclear Carbon. Nature 157, 408 (1946). https://doi.org/10.1038/157408b0

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