Sunday, December 28, 2008

chemistry in the briny deep ... sort of

When I was a graduate student I simplified a synthetic route and foolishly included an interesting conjugate addition of a cuprate. Eventually I got the details worked out, but spent quite a bit of time learning the intricacies of the voodoo that is copper chemistry. Ever since then I've read Bruce Lipshutz papers when they pop up. He has always seemed to do interesting chemistry, whether mundane or exotic, and does a halfway decent job of explaining the practical aspects of the methods.

Nothing pisses me off like some fucker publishing an incredibly skewed "new" method, that is just a rehash of someone else's work, and a quick perusal shows it is just a series of incredibly loaded substrates with no real utility.

So today I was in the midst of catching up on my reading that has piled up over the last few days, and there is a Lipshutz paper in the Org Let ASAPs for 12-23-08. It's basically about a surfactant type ligand for RCM catalysts, something I would have normally blown right by, but since it's Bruce I figured I would check it out. Nothing really struck me until I got to this:

Seawater? Hells yeah!

This has to be the stupidest/most awesome thing I've seen in a paper in a while. I can only imagine what the discussions leading up to that reaction involved.

This reaction works so well that I don't even need HPLC water, tap water works!
Screw tap water, try it in that dirty muck-filled bowl you jokingly refer to as a coffee cup.
Better yet how about in a can of Coke or a beer?

Eventually settling on something that is only just outside the line of reason.

It reminded me of a joke a long time ago between me and some post docs in the group about quenching reactions with pee. If you actually did it, how would you write it up properly? What sort of comments would acccompany the standard notebook boilerplate? "Next time clamp chair" or perhaps "I can't quench it when you're watching"?

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