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  • Things I Won't Work With

    Things I Won’t Work With: Peroxide Peroxides

    Everyone knows hydrogen peroxide, HOOH. And if you know it, you also know that it’s well-behaved in dilute solution, and progressively less so as it gets concentrated. The 30% solution will go to work immediately bleaching you out if you are so careless as to spill some on you, and the 70% solution, which I… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Dimethylcadmium

    Cadmium is bad news. Lead and mercury get all the press, but cadmium is just as foul, even if far fewer people encounter it. Never in my career have I had any occasion to use any, and I like it that way. There was an organocadmium reaction in my textbook when I took sophomore organic… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Azidoazide Azides, More Or Less

    When we last checked in with the Klapötke lab at Munich, it was to highlight their accomplishments in the field of nitrotetrazole oxides. Never forget, the biggest accomplishment in such work is not blowing out the lab windows. We’re talking high-nitrogen compounds here (a specialty of Klapötke’s group), and the question is not whethe… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Selenophenol

    This fine reagent was mentioned here (disparagingly) in the comments the other day, and I knew that it was time to add it to the list. I’ve had some other selenium entries before, and they’re all here for the same reason: their unsupportable stenches. Everyone, even people who’ve never had a chemistry class in their… Read More
  • Blog Housekeeping

    A “Things I Won’t Work With” Request

    I’ve been putting together a revised-and-expanded “Things I Won’t Work With” collection, which I hope to release first as a Kindle e-book (with other platforms following close behind). Each entry in the series has been revisited, with more useful (or not so useful) information and raised-eyebrow opinions added, and I’m… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Hexanitrohexaazaisowurtzitane

    Let’s start with the name. Quite a mouthful, isn’t it? Believe me, that one’s pretty chewy even for experienced organic chemists. We see lots of more complicated nomenclature, of course, but this one some features some speed bumps, that make you go back to make sure that you’re reading it correctly. I’ll take you throu… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Chlorine Azide

    Well, it’s been a bit too serious around here this week. So I thought today I’d step back to a period when men were men and chlorine azide was a reactive, toxic, and unstable compound that was only good for finding out what sort of explosion it would set off next. What’s that? You say… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Nitrotetrazole Oxides

    Tetrazole derivatives have featured several times here in “Things I Won’t Work With”, which might give you the impression that they’re invariably explosive. Not so – most of them are perfectly reasonable things. A tetrazole-for-carboxyl switch is one of the standard med-chem tricks, standard enough to have appeared in… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Small, Smelly Isocyanides

    Everyone’s heard of cyanide, whether they’ve spent any time in a chemistry classroom or not. And if you form a covalent bond to the carbon of that CN group, you’ve got a nitrile, and those are familiar compounds to any organic chemist. But what if you flip the group around and bond it via the… Read More
  • Things I Won't Work With

    Things I Won’t Work With: Dioxygen Difluoride

    The latest addition to the long list of chemicals that I never hope to encounter takes us back to the wonderful world of fluorine chemistry. I’m always struck by how much work has taken place in that field, how long ago some of it was first done, and how many violently hideous compounds have been… Read More
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