Silver acetate addition product with iodine

Acetyl hypoiodite (iodine acetate), CH3COOI, is prepared by treatment of silver acetate in acetic acid with iodine at room temperature [779, 780], The reagent cleaves vicinal diols to dicarbonyl compounds [779] and degrades tertiary alcohols to ketones [780], Acetyl hypoiodite is also an intermediate in the reaction of alkenes with the so-called Simonini complex, an addition product of iodine with 2 mol of silver acetate [781, 782, 783],... 

Hydrolysis of the ester does not change the configuration. The Woodward modification of the Prevost reaction is similar, but results in overall syn hydroxylation. The alkene is treated with iodine and silver acetate in a 1 1 molar ratio in acetic acid containing water. Here again, the initial product is a (3-halo ester the addition is anti and a nucleophilic replacement of the iodine occurs. However, in the presence of water, neighboring-group participation is prevented or greatly decreased by solvation of the ester function, and the mechanism is the normal Sn2 process, ... 

The prorlucts can equilibrate under the reaction conditions so that the individual yields depend on the ratio of tlie starting materials and the reaction time. Moreover, the individual product yields can be varied by the addition of one of the reaction products. Thus, addition of tris(trifluoromethyl)phosphine or iodine increases the yields of the mono- and diiodophosphines. With excess phosphorus at temperatures above 250°, the major products are phosphorus fluorides and hexa-fluoroethane (14). Results obtained under various reaction condi-tions are summarized in Table II. Since the trifluoromethyl iodide is prepared by the reaction of silver trifluoromethyl acetate with iodine, the trifluoromethylphosphines may be prepared directly from silver trifluoromethylacetate, phosphorus, and iodine (15). 

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