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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: loves2Spl00ge on November 16, 2017, 01:54:46 AM

Title: Mechanism help?
Post by: loves2Spl00ge 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!

Title: Re: Mechanism help?
Post by: clarkstill 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.