(Bis(trifluoroacetoxy)iodo)benzene

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(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 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.

References

  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.  (also in Collective Volume 8, 1993)

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