(Bis(trifluoroacetoxy)iodo)benzene

(Bis(trifluoroacetoxy)iodo)benzene
Identifiers
CAS Number	2712-78-9;
3D model (JSmol)	Interactive image;
ChemSpider	92428 ;
ECHA InfoCard	100.018.462
PubChem CID	102317;
CompTox Dashboard (EPA)	DTXSID40181584 ;
	InChI InChI=1S/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H Key: PEZNEXFPRSOYPL-UHFFFAOYSA-N ; InChI=1/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H Key: PEZNEXFPRSOYPL-UHFFFAOYAA;
	SMILES FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)c1ccccc1;
Properties
Chemical formula	C10H5F6IO4
Molar mass	430.041 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, C₁₀ H₅ F₆ I O₄, 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 cyclobutanecarboxamine 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.{{cite journal}}: CS1 maint: multiple names: authors list (link) (also in Collective Volume 8, 1993)

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[1] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link) (also in Collective Volume 8, 1993)

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