7295. Phenyliodine(III) Bis(trifluoroacetate)

Nomenclature

CAS number: 2712-78-9
Phenylbis(trifluoroacetato-κO)iodine; bis(trifluoroacetoxy)iodobenzene; iodobenzene ditrifluoroacetate; PIFA.

Description and references

Hypervalent iodine(III) reagent. Prepn: N. W. Alcock, T. C. Waddington, J. Chem. Soc. 1963, 4103; I. I. Maletina et al., J. Org. Chem. USSR 10, 294 (1974). Structural study: N. W. Alcock et al., J. Chem. Soc. Dalton Trans. 1984, 1709. Use as a one-electron oxidant: L. Eberson et al., Acta Chem. Scand. 49, 640 (1995). Review of applications in organic synthesis: G. Pohnert, J. Prakt. Chem. 342, 731-734 (2000).

Chemical structure

Properties

Crystals from chloroform + petroleum ether, mp 120-121°.

Use

In oxidation, cyclization, dehydrogenation, and dearomatization reactions.