Abstract
[57357-20-7] C16H23IO4 (MW 406.26) InChI = 1S/C16H23IO4/c1-15(2,3)13(18)20-17(12-10-8-7-9-11-12)21-14(19)16(4,5)6/h7-11H,1-6H3 InChIKey = DZKPLZUSZXYHFB-UHFFFAOYSA-N (iodine(III) reagent used as a surrogate of (diacetoxyiodo)benzene in intermolecular CN bond forming reactions through nitrene addition, CH acyloxylation, CH amination, alkene difunctionalization) Alternate Names: di-(pivaloyloxy)iodobenzene; bis(tert-butylcarbonyloxy)iodobenzene; 2,2-dimethylpropanoic acid phenyliodine complex; (di-tert-butylcarbonyloxyiodo)benzol. Physical Data: mp 104–109 °C. Solubility: soluble in CH2Cl2, CCl4, C6H6, AcOEt, MeCN, and MeOH. Form Supplied in: commercially available as a white solid. Preparative Methods: can be prepared from (diacetoxyiodo)benzene, PhI(OAc)2, by simple ligand exchange reaction with pivalic acid in chlorobenzene.1, 2 As with other bis(acyloxy)iodoarenes, the “T-shaped” structure observed in the solid state is maintained in solution. Moreover, a [1,3] sigmatropic shift of iodine between the two oxygens of the carboxylic acid ligand occurs.3 Handling, Storage, and Precautions: stable compound that can be stored at room temperature for a long period without decomposition. As with any hypervalent iodine reagent, caution is required when heating.
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