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1-Organosulfonyloxy-1, 2-benziodoxol-3-(1H)-ones (3, 4, 5) can be prepared in one step from 2-iodosobenzoic acid and the corresponding sulfonic acids. 2-carboxydiphenyliodonium salts was prepared by the acid-catalyzed condensation of 2-iodosobenzoic acid with benzene, mesitylene, and cyclohexylbenzene.
Tom Waters et. al. Experimental determination of the gas phase proton affinities of the conjugate base anions of 2-iodoxybenzoic acid (IBX) and 2-iodosobenzoic acid (IBA). Organic & Biomolecular Chemistry. 2008, 6 (14), 2530-2533.
Viktor V. Zhdankin,; Chris J. Kuehl,; Jason T. Bolz,; Mark S. Formaneck,; Angela J. Simonsen. Preparation and chemistry of 1-organosulfonyloxy-1,2-benziodoxol-3-(1H)-ones: First example of a stable adduct of 2-iodosobenzoic acid with strong acid. Tetrahedron Letters. 1994, 35 (40), 7323-7326.
Probably exists as the cyclized form 1-Hydroxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one; CAS registry no. [161-62-4].
Reagent for ɑ-hydroxylation of ketones; the by-product benzoic acid is easily removed by base extraction: Tetrahedron Lett., 25, 691 (1984). For an example, see: Org. Synth. Coll., 7, 263 (1990).
Catalyst for cleavage of toxic phosphates and reactive esters: Tetrahedron Lett., 28, 251 (1987); J. Am. Chem. Soc., 108, 788 (1986); 116, 4471 (1994).
For a review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P501c
Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant