A new mechanism of the Atherton–Todd reaction is discussed. The first step of the reaction between diesters of H-phosphonic acid and carbon tetrachloride in the presence of a base is a salt formation between carbon tetrachloride and the base [amine·Cl] ⁺ CCl ₃ ⁻ . The trichloromethanide anion [CCl ₃ ⁻ ] deprotonates dialkyl H-phosphonate to form chloroform and dialkyl phosphonate anion [(RO) ₂ P(O)] ⁻ . The latter anion reacts with the chlorine cation to furnish dialkyl chlorophosphate.
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Mitova et al. (2014) studied this question.
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