One of my favorites is Derek Lowe's write-ups on things he won't work with. Things like FOOF[1], Peroxide Peroxides[2], Azidoazide Azides[3]. The first referen

One of my favorites is Derek Lowe's write-ups on things he won't work with. Things like FOOF[1], Peroxide Peroxides[2], Azidoazide Azides[3]. The first reference is quite entertaining ... "“Being a high energy oxidizer, dioxygen difluoride reacted vigorously with organic compounds, even at temperatures close to its melting point. It reacted instantaneously with solid ethyl alcohol, producing a blue flame and an explosion. When a drop of liquid 02F2 was added to liquid methane, cooled at 90°K., a white flame was produced instantaneously, which turned green upon further burning. When 0.2 (mL) of liquid 02F2 was added to 0.5 (mL) of liquid CH4 at 90°K., a violent explosion occurred.” And he’s just getting warmed up, if that’s the right phrase to use for something that detonates things at -180C (that’s -300 Fahrenheit, if you only have a kitchen thermometer). The great majority of Streng’s reactions have surely never been run again. The paper goes on to react FOOF with everything else you wouldn’t react it with: ammonia (“vigorous”, this at 100K), water ice (explosion, natch), chlorine (“violent explosion”, so he added it more slowly the second time), red phosphorus (not good), bromine fluoride, chlorine trifluoride (say what?), perchloryl fluoride (!), tetrafluorohydrazine (how on Earth. . .), and on, and on. If the paper weren’t laid out in complete grammatical sentences and published in JACS, you’d swear it was the work of a violent lunatic. I ran out of vulgar expletives after the second page. " [1] http://blogs.sciencemag.org/pipeline/archives/2010/02/23/things_i_wont_work_with_dioxygen_difluoride http://blogs.sciencemag.org/pipeline/archives/2010/02/23/thi... [2] http://blogs.sciencemag.org/pipeline/archives/2014/10/10/things_i_wont_work_with_peroxide_peroxides http://blogs.sciencemag.org/pipeline/archives/2014/10/10/thi... [3] http://blogs.sciencemag.org/pipeline/archives/2013/01/09/things_i_wont_work_with_azidoazide_azides_more_or_less http://blogs.sciencemag.org/pipeline/archives/2013/01/09/thi...