Why Would You Do That?! – Making cyclic peroxides from triketones

Not to steal any thunder from Derek Lowes’ Things I Won’t Work With, I would like to draw attention to a paper that simply made me exclaim, “Why would you do that?!”

Selective Synthesis of Cyclic Peroxides from Triketones and H2O2

And of course the Russians are up to the most bat-sh*t insane things again. Quick primer on why this set off alarm bells: if you’re not aware, the explosive used in the 2001 shoe bomb plot was triacetone triperoxide, also known as TATP. These compounds are why chemists are taught never to wash flasks that recently contained hydrogen peroxide with acetone; the mixture easily and rapidly forms the dimeric and trimeric acetone peroxides shown to the right. Both of these explode with vigor, and should be avoided at all costs because they can literally take down planes. Want to know why you’re limited to specific volumes of liquids on planes? It’s because that’s the volume of acetone and hydrogen peroxide one would need to inflict enough damage on a jumbo jet to take it down. For those who haven’t flown in a while, it’s not much.

Peroxides of acetone. Danger! Crazy explosives!

So why in the heck were these guys making it?

The interest in the synthesis of radical
polymerization initiators and drugs gave impetus to the
development of methods for the synthesis of peroxides with
the use of carbonyl compounds, their derivatives, and H2O2
the starting reagents.

Now, maybe these aren’t so bad. The authors do report refluxing their compounds in ethanol for extended periods of time, so perhaps the extra mass and being tied up in a ring stabilizes them, but if I were a new graduate student being sold this project, I would be cautious. Remember, the authors who published on FOOF reported storing that, but I don’t think I would ever want to make it, let alone store it, so perhaps some reading between the lines is necessary for this paper.

Thoughts? Would you make these? Is it worth risking your precious, precious fingers?

Damn Russians, why do you always have to make us Americans look like wusses?