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A question about a reaction of acetal


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As the reaction shown in the figure.
I understand that acetals are quite stable unless in an acidic solution, so this reaction looks very strange to me.

I cannot think of any other acetal reactions beside acidic hydrolysis...


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I'm pretty sure that DMF DMA is a well known reagent.

For example,


and that material is the next homologue.

But that seems a rather odd reaction.



Edited by John Cuthber
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  • 5 months later...

This reactions is one of variations of Claisen Rearrangement, called Eschenmoser–Claisen rearrangement.

The Eschenmoser–Claisen rearrangement proceeds from an allylic alcohol to a γ,δ-unsaturated amide, and was developed by Albert Eschenmoser in 1964


You can see the mechanism at http://en.wikipedia.org/wiki/Claisen_rearrangement

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