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Topic: Mechanism of Schwartz's Reagent  (Read 8621 times)

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Offline g_orbital

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Mechanism of Schwartz's Reagent
« on: November 13, 2006, 10:24:12 AM »
I try to figure out the mechanism of hydrogenation from amide to imine by Schwartz's reagent (ZrHClCp2). I understand that the first intermediate is addition of the amide's oxygen to the Metal (Zr) but I don't understand how does this intermediate converts into imine.

Thank you very much indeed (Herewith attached the general scheme).

Offline movies

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Re: Mechanism of Schwartz's Reagent
« Reply #1 on: November 18, 2006, 01:38:24 PM »
When the amide attacks the Zr, it should displace the Cl, not the H, so in your second structure you should still have an H attached to the metal center.  Then it's pretty much an addition-elimination mechanism like with esterification of a carboxylic acid.  Your byproduct should be Cp2Zr=O

Offline GSK

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Re: Mechanism of Schwartz's Reagent
« Reply #2 on: January 20, 2007, 12:25:33 PM »
I don't know because I've never been able to get the Schwartz reagent to do anything for me. Never worked

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