Carbonyl Diimidazole (Slightly less dangerous phosgene)

Phosgene is a very useful molecule, but it's often not the best for the situation, and it has the unfortunate side effect of being a gas. A war gas.

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Carbonyl diimidazole isn't exactly a pussycat; by nature, it has to be very reactive. At least it's not a gas. It's a useful phosgene alternative that acts very much like an acyl chloride. It finds some use in peptide synthesis, along with various other spheres of organic chemistry.

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Is this structure correct? It's difficult to generate imidazole C-anion...

Its always worth trying this reagent if you have a difficult amide coupling; I know of two projects that were saved by CDI.