Reactivity of Naphthalimide
Dear all,
Having been out of Organic Chem for a while, I came across the following question in my research and I would be curious to hear your thoughts/explanation.
The question is whether I could convert Naphtalimide (A) to
- an imine (B), by condensation of the carbonyl with a primary amine; or
- an alkenyl (C), formed by Wittig-reaction of the carbonyl.
Although I feel thermodynamically the products should not be much less stable, I am doubting the feasibility of these reactions due to the protective nature of the imide that hinders the mechanistic intermediates. What are your thoughts? If you also deem these direct reactions problematic, any ways around this?
u/svdongen — 4 days ago