Rowe rearrangement

What is Rowe rearrangement?

The Rowe rearrangement, also called ψ-phthalazone-phthalazone rearrangement, is a chemical reaction promoted by acid and thermal conditions (120 ºC) that transforms a ψ-phthalazone (pseudo-phthalazone) into another phthalazone through N-migration of an aromatic group.

Rowe rearrangement - ψ-phthalazone-phthalazone rearrangement
Rowe rearrangement

The migratory ability of the aryl group is determined by its substituents and the nature of the substituent at the 4-position of the pseudo-phthalazone.

References

F.M. Rowe; E. Levin; A.C. Burns; J.S.H. Davies; W. Tepper “XCVI.—A new reaction of certain diazosulphonates derived from β-naphthol-1-sulphonic acid. Part I. Preparation of phthalazine, phthalazone, and phthalimidine derivatives from 4′-nitrobenzene-2-naphthol-1-diazosulphonateJ. Chem. Soc., 1926,129, 690-706

Shares