73333-99-0Relevant academic research and scientific papers
Nitrocarbons. 4. Reaction of Polynitrobenzenes with Hydrogen Halides. Formation of Polynitrohalobenzenes
Nielsen, Arnold T.,Chafin, Andrew P.,Christian, Stephen L.
, p. 4575 - 4580 (2007/10/02)
Hexanitrobenzene and pentanitrobenzene in benzene solution react with hydrogen halides (HCl, HBr, HI, but not HF) at 25 deg C to produce high yields of pentanitrohalobenzenes and 2,3,4,6-tetranitrohalobenzenes, respectively.Pentanitrofluorobenzene also reacts readily with HCl to yield 3-chloro-2,4,5,6-tetranitrofluorobenzene, but the other pentanitrohalobenzenes are much less reactive. 1,2,3,5- and 1,2,4,5-tetranitrobenzenes react rapidly with concentrated hydrochloric or hydrobromic acids at reflux to form picryl halides and 1-halo-2,4,5-trinitrobenzenes, respectively; pentanitrotoluene reacts very slowly under these conditions to form 3-halo-2,4,5,6-tetranitrotoluenes in lower yields.The scope and limitations of this regioselective reaction are defined, and comparison is made to related reactions.A mechanism is presented and discussed.
Synthesis of Polynitro Compounds. Peroxydisulfuric Acid Oxidation of Polynitroarylamines to Polynitro Aromatics.
Nielsen, Arnold T.,Atkins, Ronald L.,Norris, William P.,Coon, Clifford L.,Sitzmann, Michael E.
, p. 2341 - 2347 (2007/10/02)
Peroxydisulfuric acid in sulfuric acid solution, prepared by reaction of hydrogen peroxide with excess oleum or 100percent H2SO4, oxidizes primary polynitroarylamines and their N-acetamido derivatives to polynitro aromatics in good to excellent yields.The new procedure is illustrated by the synthesis of several new polynitro compounds, not preparable by known synthetic methods.Peroxytrifluoromethanesulfonic acid is comparably efficient for such oxidations.The scope and limitations of the new reaction have been examined and compared to other methods of synthesis of polynitro compounds.
