Aconite - 21-6-2014 at 12:33
Rxn conditions:
Excess amine in anhydrous alcohol with a ketone; ~180C.
To what extent might you expect formation of the hemiaminal ether relative to the imine?
Would the hemiaminal ether be prepared in any appreciable amount under these conditions or preferentially collapse back to the imine?
I've come across a small handful of synths that used some fancy acid catalysts, but not via direct alcoholysis of the imine. I'm guessing under basic
conditions (excess amine), the hemiaminal ether would be relatively disfavored.
Any insight is appreciated.
~Cheers