Iodoxy benzene

Benzene, iodo-, dichloride, 22, 69 Benzene, iodoso-, 22, 70 Benzene, iodoxy-, 22, 72, 73 Benzene, 1-methoxy 2 phenoxy-, 26, SO... 

Kennedy and Stock reported the first use of Oxone for many common oxidation reactions such as formation of benzoic acid from toluene and of benzaldehyde, of ben-zophenone from diphenyhnethane, of frawi-cyclohexanediol Ifom cyclohexene, of acetone from 2-propanol, of hydroquinone from phenol, of e-caprolactone from cyclohexanone, of pyrocatechol from salicylaldehyde, of p-dinitrosobenzene from p-phenylenediamine, of phenylacetic acid from 2-phenethylamine, of dodecylsulfonic acid from dodecyl mercaptan, of diphenyl sulfone from diphenyl sulfide, of triphenylphosphine oxide from triphenylphosphine, of iodoxy benzene from iodobenzene, of benzyl chloride from toluene using NaCl and Oxone and bromination of 2-octene using KBr and Oxone . Thus, they... 

N 15.17%. Three isomers are described in the literature l-Azido-2-iodoxy-benzene, brownish ndIs(from glac AcOH), expl violently by friction or on heating to 157°(Ret 1) l-Azido-3-iodoxy -benzene, brownish ndls(from w or glac AcOH) expl ca 175-80°(Ref 2) and l-Azido-4-iodoxy-benzene, crysts which rapidly become brown, expl ca 170° or on contact with coned H2S04(Ref 2)... 

A small portion of the iodosobenzene is probably oxidised to iodoxy-benzene, C6HSI02, which reacts with the hypothetical hydroxide, C6H5. I(OH)2, to give diphenyl iodonium hydroxide and iodic acid. This base is present in the alkaline filtrate from the iodosobenzene. The sulphur dioxide reduces the iodic acid to hydriodic acid, which, combining with the iodonium base, forms an iodide insoluble in cold water. 

Iodobenzene [591-50-4], C6HBI, mol wt 204.02, 62.23% I, mp —30°C, bp 188—189°C, is a colodess liquid that rapidly becomes yellow and has a characteristic odor. It is insoluble in water, but completely miscible with alcohol, chloroform, and ether. It has a density of 1.832 g/mL at 20°C and a refractive index of 1.621 at 4°C. Iodobenzene is prepared by the reaction of iodine and benzene in the presence of an oxidizing agent and from benzeneiazonium sulfate and potassium iodide (122). Iodobenzene is used as a heavy liquid for refractive index determinations, but probably its principal use is in the synthesis of iodoso compounds, RIO iodoxy compounds, RI02 and iodonium salts, R IX. 

In a 1-1. three-necked flask, protected from the light and equipped with a mechanical stirrer, an inlet tube for the introduction of chlorine (Note 1), and an exit tube carrying a calcium chloride drying tube, are placed 150 cc. of dry chloroform (Note 2) and 102 g. (0.5 mole) of iodobenzene (Org. Syn. 19, 55). The flask is cooled in an ice-salt mixture, and dry chlorine (Note 3) is introduced, as rapidly as the solution will absorb it, until an excess is present (usually about three hours is required). The yellow, crystalline iodobenzene dichloride is filtered with suction, washed sparingly with chloroform, and dried in the air on filter paper. The yield is 120-134 g. (87-94 per cent of the theoretical amount) (Notes 4 and 5). The product is quite pure and may be used directly for the preparation of iodosobenzene and iodoxy-benzene. Since iodobenzene dichloride decomposes slowly on standing, it should not be stored indefinitely. 

The iodimetric method described under iodosobenzene (p. 71) is applicable here. The main impurity in the iodoxy-benzene is iodosobenzene. 

Di-phenyl lodonium Hydroxide.—When iodoso benzene and iodoxy benzene, mixed in molecular proportions, are treated with silver hydroxide a strongly basic hydroxide compound is obtained of the formula (C6H5)2=I(OH), known as di-phenyl iodonium hydroxide. 

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