Two-headed chemical mayhem!

Tuesday, January 02, 2007

Beaker faces wrath of Dimroth rearrangement

At the end of 2006 I was messing around with some 1-alkyl-2-aminopyrimidinium-based ligands of type 1 in aqueous solution. For some reason, my ligands were giving weird NMR spectra after heating in water. Turns out Beaker the ignoramus was unaware of some old-school chemistry pioneered by Dimroth in the early 1900's, which predicts the formation of rearranged product 2. This has the alkyl group now stuck to the amino nitrogen atom rather than the pyrimidine nitrogen. The simple hydrolysis and condensation mechanism is depicted below.The reaction is very general - it can occur in a heap of nitrogen heterocycles in which an amino group is alpha to an endocyclic nitrogen atom. So yeah, its back to the drawing board for me =(



Anonymous Xray said...

Hey Beaker,

surely these things you are playing aroung with are not LIGANDS until you use them to make a metal complex!

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Anonymous Anonymous said...

I once suffered the curse known as "The Wrath of Dimroth" ... turns out it was herpes...

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Anonymous Anonymous said...

Just writing to congratulate you, your blog is quite nice to read! Keep up posting!

As for the Dimroth stuff, it's the kind of reaction that's in all "name reactions" books but that you usually overlook... until something like this happens.
Also, I have to agree a little with xray. Are those things going to be attached to some metal or are they just the building blocks for new ligands?!

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