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BarbierWieland degradation





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The Barbier–Wieland degradation is a procedure for shortening the carbon chain of a carboxylic acid by one carbon. It only works when the carbon adjacent to the carboxyl is a simple methylene bridge (analiphatic carbon with no substituents). The reaction sequence involves conversion of the carboxyl and alpha carbon into an alkene, which is then cleavedbyoxidation to convert the former alpha position into a carboxyl itself.[1][2]

Barbier-Wieland method: going from butanoic acid to propanoic acid

References

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  1. ^ Byron Riegel, Byron; Moffett, R. B.; McIntosh A. V. (1955). "nor-Desoxycholic Acid". Organic Syntheses. 24: 38; Collected Volumes, vol. 3, p. 234.
  • ^ Byron Riegel, Byron; Moffett, R. B.; McIntosh A. V. (1955). "3,12-Diacetoxy-bisnor-cholanyldiphenylethylene". Organic Syntheses. 24: 41; Collected Volumes, vol. 3, p. 237.

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    Last edited on 1 May 2023, at 16:58  





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    This page was last edited on 1 May 2023, at 16:58 (UTC).

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