[Tobian]

Dear fellow chemists,

My question to you is if it would be possible to hydrolyse the following dimer back into it's monomers. The dimer in question is the condensation product of two molecules of acetaldehyde phenylhydrazone with another molecule of acetaldehyde.

monomer : http://www.chemspider.com/Chemical-Structure.4512296.html
 
dimer is a tetrazine, a nonaromatic six membered ring (-NNCNNC-), with another 1,4 NCN bridge on top making it four tertiary amines.

Any ideas if hydrolysis of such a molecule would be possible mechanistically?

[Dan]

It should be possible, what you are looking for is aminal hydrolysis.

However, hydrolysis would give acetaldehyde and phenylhydrazine and not the hydrazone.

[Tobian]

Thanks for the quick reply. So there's no pathway back to the hydrazone and you always end up with the hydrazine and aldehydes by other intermediate products that are not the hydrazone. Or the hydrazone is maybe part of the hydrolysis and the conditions needed for aminal hydrolysis are more extreme then hydrazone hydrolysis so it will automatically hydrolyse all the way.

[Dan]

Or the hydrazone is maybe part of the hydrolysis and the conditions needed for aminal hydrolysis are more extreme then hydrazone hydrolysis so it will automatically hydrolyse all the way.

That is what I think, especially if water is present. Of course I may be wrong.