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Bouveault aldehyde synthesis

The Bouveault aldehyde synthesis (also known as the Bouveault reaction) is a one-pot substitution reaction that replaces an alkyl or aryl halide with a formyl group using a N,N-disubstituted formamide. For primary alkyl halides this produces the homologous aldehyde one carbon longer. For aryl halides this produces the corresponding carbaldehyde. The Bouveault aldehyde synthesis is an example of a formylation reaction, and is named for French scientist Louis Bouveault.

:[[File:Bouveault_Aldehyde_Synthesis_Scheme.png|500px|The Bouveault aldehyde synthesis]]

Reaction mechanism

The first step of the Bouveault aldehyde synthesis is the formation of the Grignard reagent. Upon addition of a N,N-disubstituted formamide (such as dimethylformamide) a hemiaminal is formed, which can easily be hydrolyzed into the desired aldehyde.

Variations

Variants using organolithium reagents instead of magnesium-based Grignard reagents are also considered Bouveault aldehyde syntheses.

References

References

  1. [[Louis Bouveault]]. (1904). "Modes de formation et de préparation des aldéhydes saturées de la série grasse". [[Bull. Soc. Chim. Fr.]].
  2. Louis Bouveault. (1904). "Nouvelle méthode générale synthétique de préparation des aldéhydes". Bull. Soc. Chim. Fr..
  3. Jie Jack Li. ''Name Reactions: A Collection of Detailed Reaction Mechanisms''. Springer, '''2003'''. {{ISBN. 3-540-40203-9
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

addition-reactions carbon-carbon-bond-forming-reactions formylation-reactions name-reactions
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