Click click bang bang

Mar 27, 2019
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Banert et al. recently published the first synthesis of tetraazidomethane (and some of its “exciting chemistry”). Like it’s cousin triazidomethane, this compound is highly reactive/explosive:

Safety Precautions: Tetraazidomethane (1) is extremely dangerous as a pure substance. It can explode at any time – without a recognizable cause. Less than a drop … is able to destroy completely not only the glass trap but also the vacuum Dewar flask of the cooling bath.

It looks like it’s a lot easier to make than octanitrocubane, so we’ll just have to hope that there aren’t any terrorists out there who subscribe to ACIE… (As an aside, I don’t think there are any official policies for papers that contain explosive chemical reagents, but when it comes to biological papers that contain information that could be exploited by terrorists, many journals “”http://www.pnas.org/cgi/content/full/100/10/5575">have a policy in which editors will screen and, if necessary, reject manuscripts submitted for publication if ‘an editor … conclude(s) that the potential harm of publication outweighs the potential societal benefits.’")

Though this study sounds somewhat esoteric at first, when tetraazidomethane was reacted with norbornene, the authors isolated two unexpected 5-aminotetrazole derivatives (see Scheme 2). The authors haven’t done a detailed mechanistic analysis yet, so a bit more work is needed to learn exactly what’s going on – in the meantime, I think this would be a great question to test your students’ (or friends’) arrow-pushing skills…

Joshua

Joshua Finkelstein (Senior Editor, Nature)


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