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A question about a reaction of acetal


thino
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post-104021-0-86146700-1394019667_thumb.png

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,

http://www.mn-net.com/tabid/10229/default.aspx

and that material is the next homologue.

But that seems a rather odd reaction.

 

http://en.wikipedia.org/wiki/Claisen_rearrangement#Eschenmoser.E2.80.93Claisen_rearrangement

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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