Tafel rearrangement

What is Tafel rearrangement?

The Tafel rearrangement refers to a chemical reaction that involves the electrolytic reduction of substituted acetoacetic esters using a lead cathode in alcoholic sulfuric acid (H2SO4). During the reaction, the carbon skeleton of the ester undergoes a transformation, resulting in the production of hydrocarbons that have the same number of carbon atoms as the starting material.

Tafel rearrangement
Tafel rearrangement

References

Tafel, J. and Hahl, H. (1907), Vollständige Reduktion des Benzylacetessigesters. [Complete reduction of the benzylacetoacetic ester.] Ber. Dtsch. Chem. Ges., 40: 3312-3318. https://doi.org/10.1002/cber.190704003102

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