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Desired product:

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Amide bonds absorb in the region of about 190 to 240 nm, so could using UV-C light conceivably cleave the amide bond?

Also I don't think this reaction is as simple as putting vyvanase powder under a UV-C lamp because the reaction intermediates probably need to be stabilized by a proper solvent or something, correct? What would the intermediates likely be, and what solvent would likely help?

Obviously the easiest way to get the desired product is probably simple hydrolysis, as there are not really any other hydrolyzable function groups on the starting material apart from the amide C-N bond. So this is mainly a theoretical question.


Honestly, I wouldn't bet on a cleavage here.

In principle, excited state amides and imides can undergo electron transfer reactions. We did work a bit on that (DOI) and an early example on intramolecular electron transfer between an aromatic amide and a tertiary amine, resulting in amide cleavage, was given by J.D. Coyle (PDF).

In your case, however, the situation is a bit different. You don't have an aromatic amide but an arene and an aliphatic amide. The latter aren't supposed to exhibit a strong absoption at 254 nm, see an older article by Nielsen and Schellman (DOI).

Even if you'd manage to excite the amide, I'd exclude electron transfer from one of the primary amines in your starting material and hence the cleavage of the amide.


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