Diphenyl iodonium hydroxide

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. 

Treatment with moist silver oxide gives a solution of the corresponding hydroxide dry silver oxide does not yield an oxide but decomj)oses the chloride with formation of mercury diphenyl, mercuric oxide, and silver chloride. When an acetone solution of phenylmercuric chloride is treated with a similar solution of sodium iodide, phenylmercuric iodide is formed." Arsenic trichloride heated at 100° C. for four to five hours with the chloride delds phenyl dichloroarsine. With phenyl iododichloride it yields mercuric chloride and diphenyl iodonium chloride. Ethyl mercaptan decomposes phenylmercuric chloride at 150° 0. jitlding ethyl thio-mercurie chloride, ClHg.SEt. ... 

Among the reactions of diaryliodonium salts with inorganic compounds, their hydrolysis has been studied in detail.40.41,43,51-53 jhe hydrolysis reaction proceeds quite slowly in boiling water. However, in the presence of aqueous alkali, the hydrolysis takes place in a few days for diphenyl-iodonium bromide to afford a mixture of iodobenzene, bromobenzene and phenol. With weakly nucleophilic anions, the reaction affords iodobenzene, phenol and a small amount of diphenylether. The reaction was considered to involve an unstable hydroxydiaryliodane, which is likely to be in equilibrium with diaryliodonium hydroxide. Decomposition of the hydroxyiodane leads to the... 

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