Atherton-Todd reaction

What is Atherton-Todd reaction?

The Atherton-Todd reaction was first reported in 1945 by Atherton, Openshaw and Todd. It involves the conversion of dialkylphosphite into dialkyl chlorophosphate in the presence of carbon tetrachloride and a base, typically a tertiary, secondary, or primary amine.

Atherton-Todd Reaction
Atherton-Todd Reaction

Due to the high reactivity of the formed dialkyl chlorophosphate, it cannot be isolated easily and typically reacts further with alcohols or amines to produce phosphate or phosphoramidate. As a result, only a few dialkyl chlorophosphates have been successfully isolated to date.

References

Atherton, F. R.; Openshaw, H. T. and Todd, A. R., “174. Studies on phosphorylation. Part II. The reaction of dialkyl phosphites with polyhalogen compounds in presence of bases. A new method for the phosphorylation of aminesJ. Chem. Soc., 1945, 660-663
DOI: 10.1039/JR9450000660

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