- Nitrocarbons. 4. Reaction of Polynitrobenzenes with Hydrogen Halides. Formation of Polynitrohalobenzenes
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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.
- Nielsen, Arnold T.,Chafin, Andrew P.,Christian, Stephen L.
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p. 4575 - 4580
(2007/10/02)
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