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How Can I synthesize 5,5'-dicarbaldehyde-2,2'-bipyridine from...
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+ Organic synthesis
+ Organic chemistry synthesis
+ 2-ring heterocyclic compounds
+ Synthesis of organic molecules
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Jukka Lukkari
How Can I synthesize 5,5'-dicarbaldehyde-2,2'-bipyridine from...
Hoq quote from the site "Selenium dioxide, SeO2 is an oxidizing agent generally employed in the allylic oxidation of alkenes to furnish allylic alcohols, which may be further oxidized to conjugated aldehydes or ketones" NOT METHYLARENE !
From the mechanism, the re-arrangement of the C=C in case of methylarene will be difficult due to the stability [aromaticity of the ring and SeO2 is not E+ !] on the other hand the polarity of C=N in case of methylheteroarene [containing the N] would initiate the attach of the N atom to Se thus such re-arrangement could be possible. Hope that is clear enough.
Hoq quote from the site "Selenium dioxide, SeO2 is an oxidizing agent generally employed in the allylic oxidation of alkenes to furnish allylic alcohols, which may be further oxidized to conjugated aldehydes or ketones" NOT METHYLARENE !
From the mechanism, the re-arrangement of the C=C in case of methylarene will be difficult due to the stability [aromaticity of the ring and SeO2 is not E+ !] on the other hand the polarity of C=N in case of methylheteroarene [containing the N] would initiate the attach of the N atom to Se thus such re-arrangement could be possible. Hope that is clear enough.
Hoq You have the answer already 2,9-dimethyl-1,10-phenanthroline can be oxidized [ methyl carbon is alpha to C=N] thus you can oxidize 6,6'-dimethyl-2,2'-bipyridine which has been already reported. See
---Newkome, George R. and Lee, H. W. Journal of the American Chemical Society, 105(18), 5956-7; 1983.
On the other hand 5,5'-dimethyl-2,2'-bipyridine could be oxidized to its corresponding 5,5'-dicarbaldehyde by two steps; enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. See
Hoq You have the answer already 2,9-dimethyl-1,10-phenanthroline can be oxidized [ methyl carbon is alpha to C=N] thus you can oxidize 6,6'-dimethyl-2,2'-bipyridine which has been already reported. See
---Newkome, George R. and Lee, H. W. Journal of the American Chemical Society, 105(18), 5956-7; 1983.
On the other hand 5,5'-dimethyl-2,2'-bipyridine could be oxidized to its corresponding 5,5'-dicarbaldehyde by two steps; enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. See
Hoq
quote from the site "Selenium dioxide, SeO2 is an oxidizing agent generally employed in the allylic oxidation of alkenes to furnish allylic alcohols, which may be further oxidized to conjugated aldehydes or ketones" NOT METHYLARENE !
From the mechanism, the re-arrangement of the C=C in case of methylarene will be difficult due to the stability [aromaticity of the ring and SeO2 is not E+ !] on the other hand the polarity of C=N in case of methylheteroarene [containing the N] would initiate the attach of the N atom to Se thus such re-arrangement could be possible.
Hope that is clear enough.
Good luck
Hoq
quote from the site "Selenium dioxide, SeO2 is an oxidizing agent generally employed in the allylic oxidation of alkenes to furnish allylic alcohols, which may be further oxidized to conjugated aldehydes or ketones" NOT METHYLARENE !
From the mechanism, the re-arrangement of the C=C in case of methylarene will be difficult due to the stability [aromaticity of the ring and SeO2 is not E+ !] on the other hand the polarity of C=N in case of methylheteroarene [containing the N] would initiate the attach of the N atom to Se thus such re-arrangement could be possible.
Hope that is clear enough.
Good luck
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Hoq
For the reaction mechanism of related system CH3-C=O [in your case CH3-C=N] see
---http://www.adichemistry.com/organic/organicreagents/seo2/selenium-dioxide-seo2.html
Good luck
Hoq
For the reaction mechanism of related system CH3-C=O [in your case CH3-C=N] see
---http://www.adichemistry.com/organic/organicreagents/seo2/selenium-dioxide-seo2.html
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Thanks amer...As mechanism shows that it can Oxidize C=C- CH3, why I cant 5,5-dimthyl-2,2' pyridine.? Thanks for your reply again
Thanks amer...As mechanism shows that it can Oxidize C=C- CH3, why I cant 5,5-dimthyl-2,2' pyridine.? Thanks for your reply again
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The methyl groups in bipyridyl adjacent to nitrogen atoms and it exist in a tautamerism ( H2C=C-NH ) as in methyl picoline
The methyl groups in bipyridyl adjacent to nitrogen atoms and it exist in a tautamerism ( H2C=C-NH ) as in methyl picoline
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Hoq
You have the answer already 2,9-dimethyl-1,10-phenanthroline can be oxidized [ methyl carbon is alpha to C=N] thus you can oxidize 6,6'-dimethyl-2,2'-bipyridine which has been already reported. See
---Newkome, George R. and Lee, H. W. Journal of the American Chemical Society, 105(18), 5956-7; 1983.
On the other hand 5,5'-dimethyl-2,2'-bipyridine could be oxidized to its corresponding 5,5'-dicarbaldehyde by two steps; enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. See
---Hodacova, Jana; Budesinsky, Milos, Organic Letters, 9(26), 5641-5643; 2007.
Good luck
Hoq
You have the answer already 2,9-dimethyl-1,10-phenanthroline can be oxidized [ methyl carbon is alpha to C=N] thus you can oxidize 6,6'-dimethyl-2,2'-bipyridine which has been already reported. See
---Newkome, George R. and Lee, H. W. Journal of the American Chemical Society, 105(18), 5956-7; 1983.
On the other hand 5,5'-dimethyl-2,2'-bipyridine could be oxidized to its corresponding 5,5'-dicarbaldehyde by two steps; enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. See
---Hodacova, Jana; Budesinsky, Milos, Organic Letters, 9(26), 5641-5643; 2007.
Good luck
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