Hypoiodous acid , generation

Similarly, the oxidation of iodocyclohexane by DMD under a nitrogen-gas atmosphere leads to the iodohydrin and diol as unexpected products (equation 24). The iodohydrin, formed as the major product, clearly reveals that hypoiodous acid (HOI) is generated in situ, which adds to the liberated cyclohexene. Indeed, when methyl iodide (Mel) is oxidized by DMD at subambient temperature in the presence of cyclohexene, the corresponding iodohydrin is obtained in very good yield The latter method may be utilized for the preparation of allylic alcohols with a vinylic iodo functional group from allenes (equation 25) . ... 

Hypoiodous acid (HOI), generation in dioxirane oxidation, 1158 Hypothiocyanite, from lactoperoxidase, 612... 

Iodohydrins.1 This combination (1 2) presumably generates hypoiodous acid, IOH, since it converts alkenes into iodohydrins in moderate to high yield. Bromohy-... 

The DMDO oxidation of iodocyclohexane affords lran5-2-iodocyclohexanol as the final product via intermediate formation of iodosylcyclohexane followed by elimination of hypoiodous acid, which then adds to the alkene generated in the elimination step [103]. The oxidative deiodination of iodoalkanes via conversion into iodosylalkanes followed by nucleophilic substitution of the iodosyl group has found some synthetic application, particularly in the synthesis of steroidal products (Section 3.1.19) [107]. 

Hypobromous (HOBr) and hypoiodous (IOH) acids can be generated from NaBrOs and H5IO6, respectively, by reduction with NaHSC>3 in MeCN/H20. Markovnikov orientation and awfi-stereochemistry has been observed on addition of these reagents to a variety of olefins186. 

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