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Topic: Gabriel Synthesis Starting Material  (Read 2482 times)

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Offline zsinger

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Gabriel Synthesis Starting Material
« on: October 26, 2013, 05:55:35 PM »
All,
As the wikipedia article suggests, the resonance stabilized anion of Saccarin is more stable than Pthalidomide, suggesting the possibility of synthesis of 2 and 3 prime amines………..Why is Pthalidomide still the preferred reagent, as it is more dangerous, and perhaps not as effective?  Thanks.
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Offline Altered State

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Re: Gabriel Synthesis Starting Material
« Reply #1 on: October 26, 2013, 06:18:34 PM »
I think you missnamed the compound used in Gabriel's...

The one used to make primary amines is Phthalimide: http://www.sigmaaldrich.com/catalog/product/aldrich/240230?lang=en&region=ES
which is not hazardous

And not Thalidomide http://en.wikipedia.org/wiki/Thalidomide
which is indeed very dangerous.

I don't know any compound called "Pthalidomide"

Offline zsinger

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Re: Gabriel Synthesis Starting Material
« Reply #2 on: October 26, 2013, 06:20:39 PM »
Correct…..still have the question.  Just a mis-spelling.  Thanks  ;D
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Offline Altered State

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Re: Gabriel Synthesis Starting Material
« Reply #3 on: October 26, 2013, 06:33:49 PM »
I don't see a reason why you couldn't use saccharin. In fact, it appears to had been used:
http://about.mdma.ch/000534482.html
http://pubs.acs.org/doi/abs/10.1021/ar00010a001

Why is Phtalimide prefered? I couldn't exactly tell. I guees it has to do with the price or with the easiest way to isolate products.
There is no risk asocciated to any of these 2 reagents.

If there is some other reason I would like to know it aswell

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