April 20, 2024, 04:49:51 AM
Forum Rules: Read This Before Posting


Topic: Mechanism of Schwartz's Reagent  (Read 10422 times)

0 Members and 1 Guest are viewing this topic.

Offline g_orbital

  • Regular Member
  • ***
  • Posts: 29
  • Mole Snacks: +0/-0
  • I'm a mole!
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

  • Organic Minion
  • Retired Staff
  • Sr. Member
  • *
  • Posts: 1973
  • Mole Snacks: +222/-21
  • Gender: Male
  • Better living through chemistry!
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

  • Regular Member
  • ***
  • Posts: 16
  • Mole Snacks: +1/-3
  • Gender: Male
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

Sponsored Links