Smiles rearrangement of polyfluoro substituted 2-acetylaminodiaryl ethers

Polyfluoro substituted 2-acetylaminodiaryl ethers of the type Ar_FOC₆H₄NHAc-o (II) that contain in the fluorinated ring an acceptor group, like analogs of the NH₂ group, undergo on heating in DMF the Smiles rearrangement accompanied by partial migration of the acetyl group and cyclization (in case of ethers (IIa, b)) to phenoxazine derivatives. In the case of heating in DMF, the rate constant of the rearrangement of diphenyl ether (IIa) is by an order of magnitude lower than the rate constant of the rearrangement of its analog with an NH₂ group.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 850–854, April, 1990.