Bouveault aldehyde synthesis: Difference between revisions
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The '''Bouveault aldehyde synthesis''' is a one-pot [[chemical reaction]] that converts a primary [[alkyl halide]] to an [[aldehyde]] one carbon longer.{{ | The '''Bouveault aldehyde synthesis''' is a one-pot [[chemical reaction]] that converts a primary [[alkyl halide]] to an [[aldehyde]] one carbon longer.<ref>{{cite journal | author = Bouveault, L. | journal = [[Bull. Soc. Chim. Fr.]] | year = 1904 | volume = 31 | pages = 1306}}</ref><ref>{{cite journal | author = Bouveault, L. | journal = [[Bull. Soc. Chim. Fr.]] | year = 1904 | volume = 31 | pages = 1322}}</ref> | ||
[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png | :[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png|500px|The Bouveault aldehyde synthesis]] | ||
==Reaction mechanism== | ==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|DMF]]) a [[hemiaminal]] is formed, which can easily be [[hydrolyzed]] into the desired aldehyde. | 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|DMF]]) a [[hemiaminal]] is formed, which can easily be [[hydrolyzed]] into the desired aldehyde. | ||
==See also== | ==See also== | ||
*[[Bodroux-Chichibabin aldehyde synthesis]] | *[[Bodroux-Chichibabin aldehyde synthesis]] | ||
*[[Duff reaction]] | *[[Duff reaction]] | ||
==References== | |||
<references/> | |||
*{{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 | 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.}} | |||
[[Category:Addition reactions]] | [[Category:Addition reactions]] | ||
[[Category:Carbon-carbon bond forming reactions]] | [[Category:Carbon-carbon bond forming reactions]] | ||
[[Category:Named reactions]] | |||
Latest revision as of 18:21, 27 June 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.
See also
References
- ↑ Bouveault, L. (1904). Bull. Soc. Chim. Fr. 31: 1306.
- ↑ Bouveault, L. (1904). Bull. Soc. Chim. Fr. 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:.