Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Leuckart reaction and acyloins (particularly L-PAC)
Jesse Pinkman
Harmless
*




Posts: 13
Registered: 28-8-2012
Member Is Offline

Mood: No Mood

smile.gif posted on 28-8-2012 at 13:06
Leuckart reaction and acyloins (particularly L-PAC)


Hello members of my favourite chemistry forum, I browse the forum for years, but now I have decided to register. Some of the members are truly my idols, they are "El magico" like Heisenberg on series Breaking Bad.

Now on the topic: I was searching on alternatives of the Al/Hg reductive amination of L-PAC, particularly interested in the Leuckart reaction, but I haven't seen a post or a paper if the Leuckart reaction is working on acyloins like L-PAC.

I have found a paper by Smith, Kline and French Laboratories, in which on page 312 it is written, that "benzoins behave abnormally with the Leuckart reagent".
Because benzoins are a form of acyloins, i was wondering if L-PAC will behave abnormally and undergo a cyclisation in the Leuckart reaction, not yielding the desired amino compound.

Of course one can protect the hydroxyl group but this complicates the amination.

Many thanks in advance for your responses !

Attachment: leuckart.pdf (710kB)
This file has been downloaded 436 times
View user's profile View All Posts By User
kristofvagyok
International Hazard
*****




Posts: 659
Registered: 6-4-2012
Location: Europe
Member Is Offline

Mood: No Mood

[*] posted on 28-8-2012 at 13:31


Quote: Originally posted by Jesse Pinkman  
Now on the topic: I was searching on alternatives of the Al/Hg reductive amination of L-PAC, particularly interested in the Leuckart reaction, but I haven't seen a post or a paper if the Leuckart reaction is working on acyloins like L-PAC.

I have found a paper by Smith, Kline and French Laboratories, in which on page 312 it is written, that "benzoins behave abnormally with the Leuckart reagent".


I would suggest to find a bit more interesting and less harmless part of chemistry than making aint so legal things with basic reactions -what won't work in this case.

Also. Here is something interesting for you:
Journal fuer Praktische Chemie (Leipzig), 1890 , vol. <2>41, p. 327




I have a blog where I post my pictures from my work: http://labphoto.tumblr.com/
-Pictures from chemistry, check it out(:

"You can’t become a chemist and expect to live forever."
View user's profile Visit user's homepage View All Posts By User
Lambda-Eyde
International Hazard
*****




Posts: 856
Registered: 20-11-2008
Location: Norway
Member Is Offline

Mood: Cleaved

[*] posted on 31-8-2012 at 08:31


Quote: Originally posted by kristofvagyok  

Also. Here is something interesting for you:
Journal fuer Praktische Chemie (Leipzig), 1890 , vol. <2>41, p. 327

Seeing this aroused my interest, so I tried to check it out - but if I understand the German correctly, you have provided the wrong page number. "Einwirkung von Ammoniumformiat auf Benzoin" appears on page 333 in the article "Ueber die Einwirkung von Ammoniumformiat auf Ketone" written by mr. Leuckart himself. DOI: 10.1002/prac.18900410121

Uploaded for those who can read German.

Attachment: Ueber die Einwirkung Ammoniumformiat auf Ketone J.Pr.Chemie 41 1890.pdf (486kB)
This file has been downloaded 513 times





This just in: 95,5 % of the world population lives outside the USA
You should really listen to ABBA
Please drop by our IRC channel: #sciencemadness @ irc.efnet.org
View user's profile View All Posts By User
zed
International Hazard
*****




Posts: 2244
Registered: 6-9-2008
Location: Great State of Jefferson, City of Portland
Member Is Offline

Mood: Semi-repentant Sith Lord

[*] posted on 12-9-2012 at 12:59


If you had some L-PAC, it could easily be reduced to the diol.

That diol could then be refluxed with dilute Sulfuric Acid, to yield P2P.
View user's profile View All Posts By User
Jesse Pinkman
Harmless
*




Posts: 13
Registered: 28-8-2012
Member Is Offline

Mood: No Mood

smile.gif posted on 25-9-2012 at 09:48



Quote:

If you had some L-PAC, it could easily be reduced to the diol. That diol could then be refluxed with dilute Sulfuric Acid, to yield P2P.

I'm interested in ephedrines, not in Phenyl-2-Propanones

But for those interested in P2P : The same fermentation which produces L-PAC, can also produce the diol, then a simple Pinacol rearrangement will turn it into P2P

Here is the reference:

Attachment: diol.pdf (831kB)
This file has been downloaded 897 times
View user's profile View All Posts By User

  Go To Top