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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: g_orbital on November 13, 2006, 10:24:12 AM

Title: Mechanism of Schwartz's Reagent
Post by: g_orbital 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).
Title: Re: Mechanism of Schwartz's Reagent
Post by: movies 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
Title: Re: Mechanism of Schwartz's Reagent
Post by: GSK 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