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Author: Subject: DMF in Leuckart reaction?
Oboe
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[*] posted on 31-10-2008 at 04:28
DMF in Leuckart reaction?


It's well known that formamide and N-methylformamide can be used in the Leuckart reaction but I've never seen any references where DMF (N,N-dimethylformamide) is used.

I'm particularly interested in using DMF to introduce an -NMe2 group to an aliphatic aldehyde? If someone has any more information about this then please feel free to share.
Thanks!
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Bronstein
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[*] posted on 31-10-2008 at 13:26


In Organic Reactions volume 5 there is a review on the leuckart reaction (I think there is a scan of that chapter somewhere on the internet). There is an example of an experimental procedure using DMF, with furfural as the aldehyde. Not an aliphatic aldehyde, but still.

It seems that you get the desired amine directly when using DMF, no need to hydrolise the amide that forms otherwise.
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Sauron
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[*] posted on 1-11-2008 at 01:02


I will look that one up, because N,N-simethylfurcurylamine is useful for certain nefarious purposes that I like to track.

Like rearranging to N-methyl-3-hydroxypiperidine. Ditran precursor.




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Oboe
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[*] posted on 2-11-2008 at 11:32


Quote:
Originally posted by Bronstein
In Organic Reactions volume 5 there is a review on the leuckart reaction (I think there is a scan of that chapter somewhere on the internet). There is an example of an experimental procedure using DMF, with furfural as the aldehyde. Not an aliphatic aldehyde, but still.

It seems that you get the desired amine directly when using DMF, no need to hydrolise the amide that forms otherwise.


Thanks. I found that chapter here but has page missing (Table I) which would give me the information I need. Anyone have this page p325? Why would someone leave it out? :mad::(
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