A new synthetic method of preparing iodohydrin and bromohydrin derivatives through in situ generation of hypohalous acids from H5IO6 and NaBrO3 in the presence of NaHSO3

Organic compounds having carbon-carbon double bonds react with H5IO6 or NaBrO3 in the presence of NaHSO3, producing iodohydrin and bromohydrin derivatives in good yields. This preparation involves the in situ generation of respective hypohalous acids from H5IO6 and NaBrO3 in the presence of NaHSO3. Iodohydroxylation exhibits high stereroselectivity while bromohydroxylation shows no stereoselectivity. Alkynes react with H5IO6/NaHSO3 producing ketones, and reaction with NaBrO3/NaHSO3 produces alpha, alpha-dibromo ketones.