March 29, 2024, 03:01:15 AM
Forum Rules: Read This Before Posting


Topic: Mechanism help?  (Read 1895 times)

0 Members and 1 Guest are viewing this topic.

Offline loves2Spl00ge

  • New Member
  • **
  • Posts: 7
  • Mole Snacks: +0/-0
Mechanism help?
« on: November 16, 2017, 01:54:46 AM »
Do the nonbonding lone pairs on the alcohol donate into the pi system next to it to make it grab the vinyl ether? I'm also confused on what the mercury acetate does before the Claisen rearrangement.

Thanks!

Offline clarkstill

  • Chemist
  • Full Member
  • *
  • Posts: 476
  • Mole Snacks: +77/-4
Re: Mechanism help?
« Reply #1 on: November 16, 2017, 06:55:57 AM »
Are you able to draw the mechanism for a general Claisen rearrangement? If so, you should be able to work back from the product to work out the intermediate you need to form.

As for the role of the mercury, there is a similar mechanism discussed by Overman here:

http://pubs.acs.org/doi/pdf/10.1021/ja00809a054

It seems the mercury forms a mercurinium ion with the enol ether, accelerating addition of the alcohol to form the key enol ether species.


Sponsored Links