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By Gould R.F. (ed.)

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Reactivity of H-Phosphonates with the trichloromethanide anion. The catalytic cycle is completed with the reaction of this trichloromethanide anion with monomethyl H-phosphonate to form chloroform and the monoalkyl H-phosphonate anion. The latter anion can then react with a further molecule of dialkyl H-phosphonate in a new catalytic cycle. 1. The key result of these calculations is that the computations support the suggestion that the catalytically active trivalent phosphorus (III) species will be present in those reactions that involve both the diesters of H-phosphonic acid and the monomethyl H-phosphonate anion.

The esters of phosphonic acid bearing a P–C bond are thus more susceptible to alkaline hydrolysis than the phosphate esters. The P–C bond is usually stable to hydrolytic cleavage. -Hydroxyalkylphosphonates are an exception. In the presence of an alkali, they undergo rearrangement to give phosphate with cleavage of the P–C bond. Addition to unsaturated compounds (Pudovik reaction) H-phosphonate diesters react with electrophilic unsaturated compounds under basic conditions with the formation of dialkyl alkylphosphonic acids [136–139].

Although the possibility of a stepwise mechanism involving the intermediacy of a solvated zwitterionic intermediate cannot be completely ruled out in aqueous solution, these gas-phase calculations [22] together with the experimental data-based results of Guthrie [21] give a strong indication that the concerted addition of water to phosphoryl compounds is probably the major reaction channel under the conditions of their acid or neutral hydrolysis. 5 ACIDOLYSIS The acidolysis of dimethyl H-phosphonate to phosphonic acid was studied recently by 1 H- NMR and 31P{H} NMR spectroscopy [27].

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