(Bis(trifluoroacetoxy)iodo)benzene
iodo)benzene.png) | |
iodo)benzene-3D-balls.png) | |
| Names | |
|---|---|
| Other names
Phenyliodine bis(trifluoroacetate); PIFA | |
| Identifiers | |
2712-78-9  | |
| ChemSpider | 92428  |
| Jmol interactive 3D | Image |
| PubChem | 102317 |
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| Properties | |
| C10H5F6IO4 | |
| Molar mass | 430.04 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
(Bis(trifluoroacetoxy)iodo)benzene, C10H5F6IO4, is a hypervalent iodine compound used as a reagent in organic chemistry. The reagent is used in an acidic modification of the Hofmann rearrangement. One example is the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride.[1] It also brings around the conversion of a hydrazone to a diazo compound, for example in the diazo-thioketone coupling. It also converts thioacetals to their parent carbonyl compounds.
Preparation
The syntheses of all aryl hypervalent iodine compounds start from iodobenzene. The compound can be prepared by reaction of iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid. The method is analogous to the synthesis of diacetoxyiodobenzene (C6H5I(OAc)2) which uses a mixture of peracetic acid and acetic acid.
References
- ↑ Almond, M. R.; Stimmel, J. B.; Thompson, E. A.; Loudon, G. M. (1988). "Hofmann Rearrangement Under Mildly Acidic Conditions Using [I,I-Bis(Trifluoroacetoxy)]Iodobenzene:Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide". Organic Syntheses 66: 132. doi:10.15227/orgsyn.066.0132. (also in Collective Volume 8, 1993)