Département de chimie moléculaire

Abstract [536-80-1] C6H5IO (MW 220.01) InChI = 1S/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H InChIKey = JYJVVHFRSFVEJM-UHFFFAOYSA-N (oxygen atom transfer to ketones, metal-catalyzed oxygen atom transfer to alkenes, formation of alpha-diketones, bridgehead triflates, alpha,alpha,beta-unstaturated lactones and ketones, alpha-hydroxy-methyl acetals, alpha-keto triflates, alpha-hydroxy ketones, C-C coupling, oxidation of amines, azidation, metal-catalyzed alkene aziridination and difunctionalization, C-H amination, imination of sulfides and sulfoxides, carbene transfer, metal-free C-N bond forming reaction)
Alternate Name: iodosobenzene. Physical Data: mp 210 °C with decomposition (explodes); polymeric. Solubility: slightly soluble in H₂O, MeOH. In MeOH the reagent is PhI(OMe)₂. Both solvents, as well as CH₂Cl₂, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), 2,2,2-trifluoroethanol (TFE) and MeCN, are used for reactions. Form Supplied in: white to slightly yellow solid from synthesis. Preparative Methods: prepared as a white solid by base hydrolysis of commercially available (Diacetoxyiodo)benzene in 75% yield. Purifications: washing the solid with CHCl₃ to remove traces of PhI. The material is obtained in about 99{%} purity as determined iodometrically. Caution should be taken when drying PhIO to remove traces of solvent: this must be made at room temperature under vacuum. 3g of PhIO have been reported to explode upon drying over toluene (110 °C, 0.1 torr). Handling, Storage, and Precautions: refrigeration should be used for long-term storage, since extended storage at room temperature leads to disproportionation of PhIO thereby producing a mixture of PhI and the explosive PhIO₂.