Bouveault aldehyde synthesis: Difference between revisions
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*{{cite journal | author = Smith, L. I.; 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}} | *{{cite journal | author = Smith, L. I.; 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}} | ||
* {{cite journal | journal = [[J. Am. Chem. Soc.]] | year = 1953 | volume = 75 | pages = 3697 | doi = 10.1021/ja01111a027 | author = Sice, Jean}} | * {{cite journal | journal = [[J. Am. Chem. Soc.]] | year = 1953 | volume = 75 | pages = 3697 | doi = 10.1021/ja01111a027 | author = Sice, Jean | title = Preparation and Reactions of 2-Methoxythiophene}} | ||
* {{cite journal | journal = [[J. Chem. Soc.]] | year = 1958 | pages = 1054 | 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 | doi = 10.1039/jr9580001054 | title = 210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons | author = Jones, E. R. H.}} | ||
Revision as of 18:10, 23 February 2009
The Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer.[1][2]
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 DMF) a hemiaminal is formed, which can easily be hydrolyzed into the desired aldehyde.
References
- ↑ Bouveault, L. (1904). Bull. Soc. Chim. France 31: 1306.
- ↑ Bouveault, L. (1904). Bull. Soc. Chim. France 31: 1322.
- Smith, L. I.; Nichols, J. (1941). "The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes". J. Org. Chem. 6: 489. doi:.
- Sice, Jean (1953). "Preparation and Reactions of 2-Methoxythiophene". J. Am. Chem. Soc. 75: 3697. doi:.
- Jones, E. R. H. (1958). "210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons". J. Chem. Soc.: 1054. doi:.