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Topic: Acetamide + P4O10 -> nitrile  (Read 12337 times)

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Garneck

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Acetamide + P4O10 -> nitrile
« on: October 21, 2005, 03:57:46 PM »
I rarely ask questions here, but I've got a problem that's not even mine.

Can anyone tell me something about the mechanism of the reaction of acetamide with P4O10 to form a nitrile?

I know this reaction with SOCl2, but I can't find anything that says something about using P4O10.
Thanks :)

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Re:Acetamide + P4O10 -> nitrile
« Reply #1 on: October 21, 2005, 05:41:44 PM »
Same idea as the thionyl chloride reaction.  P4O10 is a powerful dehydrating agent.  So, the amide oxygen attacks phosphorus to make an imidate.  There is a proton transfer step, and then the remaining lone pair on the nitrogen moves down to eject the oxygen and form a protonated nitrile.  Another proton transfer step and your done.  Basically, P4O10 wants to end up as phosphoric acid, H3[/sup]PO4.

Garneck

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Re:Acetamide + P4O10 -> nitrile
« Reply #2 on: October 22, 2005, 02:00:49 AM »
Thank you movies. That was just what I was thinking, thanks for your confirmation! :)

laotree

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Re:Acetamide + P4O10 -> nitrile
« Reply #3 on: October 29, 2005, 07:16:44 PM »
Check ecompound.com, reaction reference, reaction mechanism. Morgan-Walls reaction and Simonis reaction mechanism could give you some hints.

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