I'm learning that enolates are stronger than enamines are stronger than enols in terms of general nucleophilicity. Makes sense. But what I can't find any explanation for online is why the trend shouldn't keep on going past enolates. Why isn't there a name for the species of enamine deprotonated on its heteroatom the same way there is for enols? (enols -> enolates, enamines -> ?)

enter image description here

I would imagine this species does not exist for some reason having to do with stability. Any explanation or reasoning would be greatly appreciated and would help me get into the subject more. Thanks.


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.