Barbier-Wieland degradation

What is Barbier-Wieland degradation?

The Barbier-Wieland degradation method is a stepwise process used for the degradation of aliphatic carboxylic acids, particularly in sterol side chains, to the next lower homolog.

To achieve this, the ester is first converted to a tertiary alcohol, which is then dehydrated with acetic anhydride. Next, the resulting olefin is oxidized with chromic acid to yield a lower homologous carboxylic acid.

This method is useful in various chemical applications, particularly in the analysis of sterol side chains. By degrading the carboxylic acid chain in a stepwise manner, the resulting lower homolog can be identified and analyzed for its properties and potential applications.

Barbier-Wieland degradation
Barbier-Wieland degradation

References

  • Wieland, H. (1912), Über Hydrierung und Dehydrierung. [On hydrogenation and dehydrogenation.] Ber. Dtsch. Chem. Ges., 45: 484-493. https://doi.org/10.1002/cber.19120450171
  • P. Barbier and R. Locquin, “Method of decomposing various saturated mono- and dibasic acids” Comptes Rend. 156, 1443-1446 (1913)
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