Reduction ofo-iodosobenzoate ion by sulfides and its oxidative regeneration

o-Iodosobenzoate and o-iodoxybenzoate ion (IBA and IBX, respectively) are turnover catalysts of hydrolyses of phosphonofluoridates and non-toxic simulants. Reactions of IBA with phosphonothioates are stoichiometric because sulfides (e.g. 4-methoxybenzenethiol) reduce IBA to o-iodobenzoate ion. Oxidants, e.g. , as OXONE, and magnesium peroxyphthalate, MPPA, regenerate IBA and gradually oxidize it to IBX, which eventually decomposes. The procedure was tested on hydrolyses of p-nitrophenyl diphenylphosphate (pNPDPP) and 4-nitrobenzenesulfonyl fluoride, 1, catalyzed by IBA, and the catalyzed hydrolysis of 1 was examined. Some of the oxidation products of 4-methoxybenzene thiol were identified by 1H NMR spectroscopy and oxidative decomposition of IBX was monitored. Periodate ion slowly oxidized o-iodobenzoate ion to IBA and IBX.