3
$\begingroup$

I was asked to solve this problem, and the answer key shows this:

molecule

I'm not sure what's going on here, but it looks like some sort of a rearrangement and reduction. Is it an internal reaction between the ether and the alkene?

$\endgroup$
3
$\begingroup$

This is an example of the Claisen rearrangement. It is basically the oxa-analogue of the Cope rearrangement. The Claisen rearrangement can occur with aromatic or non-aromatic allyl vinyl ethers. The reaction mechanism involves a concerted, intramolecular, [3,3]-sigmatropic rearrangement. In the aromatic case, the rearrangement is followed by a proton shift (keto-enol tautomerization) to yield the final product with the aromaticity restored.

Here's a diagram of the aromatic Claisen rearrangement

enter image description here

Here's a diagram for the non-aromatic counterpart.

enter image description here

$\endgroup$
  • $\begingroup$ From the historical perspective, the Cope rearrangement is a carbon analog of the Claisen rearrangement. ;) $\endgroup$ – user55119 Feb 24 at 23:34

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.