5
$\begingroup$

In a reaction between an aliphatic primary amine and a ketone, I could expect a ketimine as a product or intermediate. My question regards tautomerization of this intermediate: has tautomerization between the two possible imine structures ever been observed, or is even possible? I tried to search imine tautomerism and transamination, but I can't find what I'm looking for. I imagine this would be a simple experiment to conduct, but I can't find anything in the literature on this.

Proposed ketimine tautomerism

Improve this question
$\endgroup$
1
  • 5
    $\begingroup$ Yes, this is common. One example is enzyme catalyzed transamination reactions that utilize pyridoxal phosphate as a cofactor. $\endgroup$
    – Andrew
    Commented Feb 4, 2021 at 21:30

1 Answer 1

Reset to default
3
$\begingroup$

I found something very similar to what I sought in Dose, Nature 179, 734 (1957) though it involves aldimines and a decarboxylation step. The author gives a very well explained mechanism for the process and reports varying transamination ratios of valine based on the substitution of the aldehyde. An example:

enter image description here

Improve this answer
$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.