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Koser S Reagent Synthesis Essay

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Abstract

InChI = 1/C13H13IO4S/c1-11-7-9-13(10-8-11)19(16,17)18-14(15)12-5-3-2-4-6-12/h2-10,15H,1H3

InChIKey = LRIUKPUCKCECPT-UHFFFAOYAS

(reagent for the phenyliodination and oxytosylation of various functional groups;4 excellent Hofmann reagent;16 useful for bis-lactonizations,7 oxidations and oxidative transformations20)

Alternate Name: HTIB; Koser's reagent; phenyliodine(III) (hydroxyl)tosylate.

Physical Data: nearly colorless crystalline solid (pale ‘yellow’ cast); 140–142 °C,2 136–138.5 °C.3

Solubility: insoluble in Et2O; largely insoluble in CH2Cl2, CHCl3, MeCN (rt); moderately soluble in H2O; soluble in MeCN (reflux), MeOH, DMSO.

Form Supplied in: white solid; commercially available in 96% purity.

Preparative Methods: conveniently prepared by the treatment of (Diacetoxyiodo)benzene/MeCN mixtures with warm solutions of p-Toluenesulfonic Acid in MeCN. When the acid is introduced, PhI(OAc)2 ‘dissolves’ to give deep yellow solutions from which HTIB readily separates. If the reaction mixtures are kept near the reflux temperature, the crystallization of HTIB from the solvent can be controlled. At lower temperatures, HTIB separates more rapidly but can, if necessary, be recrystallized by heating the final mixtures of dissolution or from fresh MeCN. Preparations of HTIB can be readily conducted on 50–100 g scale.

Handling, Storage, and Precautions: a fairly stable compound which may be stored at rt; for extended storage, keep refrigerated in a dark bottle.