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.
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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Whew. This one's a little embarassing. One of my favorite things about organic chemistry is just how much it's like Lego. Molecules that seem like indecipherable structures to the uninitiated start looking more and more like a bunch of building blocks. It's been said that organic chemistry is the…
Here is another molecule that's gone out of favor in recent decades: carbon tetrachloride:
Chlorinated solvents are great solvents. Something about the polarizability, medium polarity, (relative) lack of reactivity, just makes them the only thing that will work in a lot of applications. The three…
One of my best friends in undergrad, upon learning about the use of acetal protecting groups for carbonyls, exclaimed, "they're like ketone condoms!" Indeed. Protecting groups are ubiquitous in organic synthesis, and another one you see all the time is Boc, which is used to protect amines:
Boc2O,…
Automated solid-phase synthesis of biomolecules defines 20th century biology. I previously covered a protecting group that is ubiquitous in DNA synthesis, but the Nobel was actually awarded for peptide chemistry.
Fmoc is sort of to amino acids what DMT is to DNA. In amino acid synthesis, you take…
Is this structure correct? It's difficult to generate imidazole C-anion...
Fixed, thanks.
Its always worth trying this reagent if you have a difficult amide coupling; I know of two projects that were saved by CDI.