A question about a reaction of acetal

[thino]

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...

 

[rktpro]

Bewildering. I wonder how the reagent exists: 3 lone pair containing atoms on tetrahedral carbon. I can't think of reaction mechanism. Someone else will enlighten us.

[hypervalent_iodine]

I had a look at this when it was posted and couldn't make heads or tails of it either! I might sit down and have a better look when I have time.

[John Cuthber]

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 March 12, 2014 by John Cuthber

[crimsonpetal]

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