R-Butyl hypoiodite

An alternative method for the formation of acyl hypoiodites, developed by Barton, involves the treatment of the acid with r-butyl hypoiodite. Subsequent white light photolysis in benzene at room temperature gave good yields of it ides from primary, secondary and tertiary acids (equation 21). The method was not applicable in the presence of alcohols. A more recent technique involving hypervalent iodine is due to Suarez primary, secondary or tertiary aliphatic acids are heated to reflux in tetrachloromediane with iodosylbenzene diacetate and iodine resulting in good yields of iodides. The method is mild and, with obvious exceptions such as unprotected alcohols, is tolerant of many functional groups, as illustrated in equation (22). ... 

Decarboxylation Benzoic anhydride. N-Bromosuccinimide. r-Butylhydroperoxide. r-Butyl-hypoiodite. Copper chromate. Copper powder. Copper salts. Cuprie carbonate. N,N-Di-methylanilrne. N,N-Dimethyl-p-toluidine see Potassium permanganate, reference 32). Lead dioxide. Lead tetraacetate. Lithium iodide dihydrate. Potassium fluoride. Quinoline. Sodium hypochlorite. 

Decarboxylation. A benzene solution of a carboxylic acid and f-butyl hypoiodite presumably contains an equilibrium amount of r-butanol and the acyl hypoiodite, which on illumination decomposes to the alkyl iodide and CO ... 

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