[racemiz.er]

Okay, this is a tricky one... more of a thinker's question!

So, I was studying some imine formations. I was wondering if a tautomerism of imine is possible on the nitrogen end.



Any ideas guys?

[hollytara]

Yes - imines can easily tautomerize. 

But the one you show it is disfavored - double bond better next to aromatic ring and double bond better if NOT exocyclic to cyclohexane.

Often an amine / carbonyl is used that forms an exocyclic double bond so as to favor isomerization to the endocyclic, which then reacts predictably. 

[rolnor]

This is true for enamines, not imines. Enamines can form iminium salts. You need a secondary amine to get a enamine.

[racemiz.er]

Yes - imines can easily tautomerize. 

But the one you show it is disfavored - double bond better next to aromatic ring and double bond better if NOT exocyclic to cyclohexane.

Often an amine / carbonyl is used that forms an exocyclic double bond so as to favor isomerization to the endocyclic, which then reacts predictably.

Ummm... basically the cyclohexyl amine is a part of a cis isomeric cyclohexane ring. Do you have any suggestions for making it trans? Basically i am trying to invert cis 1,4 substituted cylohexane to trans 1,4 substituted cyclohexane

[rolnor]

You dont get the double bond on the cyclohexane, thats wrong. What substituents do you have on the ring? Its probably no problem to invert.

[racemiz.er]

You dont get the double bond on the cyclohexane, thats wrong. What substituents do you have on the ring? Its probably no problem to invert.

Hydroxy on para position. Unsure on how to invert. Is there a chemical process for inversion (not substitution)?

[kriggy]

Mitsunobu is usually used for this. react it with acetic acid and then hydrolyze the ester and you get inversion

[rolnor]

And that is substitution!