Bouveault aldehyde synthesis: Difference between revisions
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*{{cite journal |author1=Smith, L. I. |author2=Nichols, J. | title = The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes | journal = [[J. Org. Chem.]] | year = 1941 | volume = 6 | pages = 489 | doi = 10.1021/jo01204a003 | issue = 4}} | *{{cite journal |author1=Smith, L. I. |author2=Nichols, J. | title = The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes | journal = [[J. Org. Chem.]] | year = 1941 | volume = 6 | pages = 489 | doi = 10.1021/jo01204a003 | issue = 4}} | ||
* {{cite journal | journal = [[J. Am. Chem. Soc.]] | year = 1953 | volume = 75 | pages = 3697–3700 | doi = 10.1021/ja01111a027 | author = Sice, Jean | title = Preparation and Reactions of 2-Methoxythiophene | issue = 15}} | * {{cite journal | journal = [[J. Am. Chem. Soc.]] | year = 1953 | volume = 75 | pages = 3697–3700 | doi = 10.1021/ja01111a027 | author = Sice, Jean | title = Preparation and Reactions of 2-Methoxythiophene | issue = 15| bibcode = 1953JAChS..75.3697S }} | ||
* {{cite journal | journal = [[J. Chem. Soc.]] | year = 1958 | pages = 1054–1059 | doi = 10.1039/jr9580001054 | title = 210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons | author = Jones, E. R. H.}} | * {{cite journal | journal = [[J. Chem. Soc.]] | year = 1958 | pages = 1054–1059 | doi = 10.1039/jr9580001054 | title = 210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons | author = Jones, E. R. H.}} | ||
{{Organic reactions}} | {{Organic reactions}} | ||
Latest revision as of 12:09, 24 June 2025
Template:Reactionbox 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.[1][2] 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.
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.[3]
See also
References
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- ↑ Jie Jack Li. Name Reactions: A Collection of Detailed Reaction Mechanisms. Springer, 2003. Template:ISBN
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