Bouveault aldehyde synthesis - Revision history

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	~~[[id:Sintesis aldehida Bouveault]]~~
	~~[[ja:ブーボーのアルデヒド合成]]~~

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	==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==
			*[[Bodroux-Chichibabin aldehyde synthesis]]
			*[[Duff reaction]]

	==References==		==References==
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	* {{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. 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.}}

	~~==See also==~~
	*[[Bodroux-Chichibabin aldehyde synthesis]]
	*[[Duff reaction]]

	[[Category:Addition reactions]]		[[Category:Addition reactions]]

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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.<ref>{{cite journal \| author = Bouveault, L. \| journal = [[Bull. Soc. Chim. ~~France~~]] \| year = 1904 \| volume = 31 \| pages = 1306}}</ref><ref>{{cite journal \| author = Bouveault, L. \| journal = [[Bull. Soc. Chim. ~~France~~]] \| year = 1904 \| volume = 31 \| pages = 1322}}</ref>		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\|500px\|The Bouveault aldehyde synthesis]]		:[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png\|500px\|The Bouveault aldehyde synthesis]]

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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.}}

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2009-02-23T18:09:08Z

Citation maintenance. Formatted: author, doi, title. You can use this bot yourself! Please report any bugs.

← Older revision		Revision as of 18:09, 23 February 2009
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	<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 \| 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}}		* {{cite journal \| journal = [[J. Am. Chem. Soc.]] \| year = 1953 \| volume = 75 \| pages = 3697 \| doi = 10.1021/ja01111a027 \| author = Sice, Jean}}
	* {{cite journal \| journal = [[J. Chem. Soc.]] \| year = 1958 \| pages = 1054}}		* {{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.}}

	==See also==		==See also==

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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.{{~~Ref~~\|~~Bouveault1904~~}}		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. France]] \| year = 1904 \| volume = 31 \| pages = 1306}}</ref><ref>{{cite journal \| author = Bouveault, L. \| journal = [[Bull. Soc. Chim. France]] \| year = 1904 \| volume = 31 \| pages = 1322}}</ref>

	[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png~~\|center~~\|500px\|The Bouveault aldehyde synthesis]]		:[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png\|500px\|The Bouveault aldehyde synthesis]]

	==Reaction mechanism==		==Reaction mechanism==

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	==References==		==References==
	# {{~~Note~~\|~~Bouveault1904}} Bouveault, L. ''Bull. Soc. Chim. France'' '''1904''', ''31'', 1306 & 1322.~~		<references/>
	# Smith, L. I.; Nichols, J. ''[[J. Org. Chem.]]~~'' '''~~1941~~''', ''~~6~~'',~~ 489.		*{{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}}
	~~# Sicé, J. ''~~[[J. Am. Chem. Soc.]]~~'' '''~~1953~~''', ''~~75~~'',~~ 3697.		* {{cite journal \| journal = [[J. Am. Chem. Soc.]] \| year = 1953 \| volume = 75 \| pages = 3697}}
	~~# Jones, E. R. H. ''et al.'' ''~~[[J. Chem. Soc.]]~~'' '''~~1958~~''',~~ 1054.		* {{cite journal \| journal = [[J. Chem. Soc.]] \| year = 1958 \| pages = 1054}}

	==See also==		==See also==

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			[[id:Sintesis aldehida Bouveault]]
	[[ja:ブーボーのアルデヒド合成]]		[[ja:ブーボーのアルデヒド合成]]