Phenyliodine(III) Bis(trifluoroacetate)

[2712-78-9] C10H5F6IO4 (MW 430.05) 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 InChIKey = PEZNEXFPRSOYPL-UHFFFAOYSA-N (cyclopropyl groups undergo ring opening,2 alkynes are cleaved,3 phenols are oxidized to quinones4-8 and in some cases oxidative intramolecular coupling occurs,9-13 ketones yield α-hydroxy ketones,14 certain β-diketones undergo cyclization,15 Pummerer-type reaction occurs,16 and deprotective dethioacetalization is an important use17) Alternate Names: bis(trifluoroacetoxyiodo)benzene; iodobenzene bis(trifluoroacetate); PIFA; BTI. Physical Data: mp 121–125 °C. Solubility: sol CH2Cl2, CCl4, CF3CH2OH, (CF3)2CHOH. Form Supplied in: white solid; commercially available. Polymersupported reagent eases purification from the iodoarene.20 A recyclable adamantane based reagent is prepared in two steps from commercially available starting material.21 Preparative Method: can be synthesized by reaction of (Diacetoxyiodo)benzene with Trifluoroacetic Acid.18 Prepared from (a) anhydrous percabonate phenyl iodide and TFA; (b) phenyl iodide, K2S2O8, and TFA.22 Handling, Storage, and Precautions: moisture sensitive; irritant.