The haloform reaction is:

$$\ce{RCOCH3 +3X2 +4OH^- -> RCOO^- +CHX3 + 3X- + 3H2O}$$ where, $\ce{X}$ is $\ce{Cl}$, $\ce{Br}$, or $\ce{I}$. However, I was wondering if this reaction works with fluorine and pseudohalogens? For instance would the following reactions occur? $$\ce{RCOCH3 +3N2O4 +4OH^- -> RCOO^- +CH(NO2)3 + 3NO2- + 3H2O}$$ $$\ce{RCOCH3 +3(CN)2 +4OH^- -> RCOO^- +CH(CN)3 + 3CN- + 3H2O}$$

  • $\begingroup$ Trinitromethane, $\ce{CH(NO2)3}$ is a potent oxidizer and tend to explode on long standing. $\endgroup$ – Nilay Ghosh Feb 25 '18 at 2:27
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    $\begingroup$ @NilayGhosh I know, that's partially why I asked this question, I was wondering if trinitromethane can be produced via the haloform reaction. Especially as it's also referred to as nitroform apparently. $\endgroup$ – tox123 Feb 25 '18 at 3:39
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    $\begingroup$ Nitroformate would be fine as a leaving group, but you would probably need a source of NO2+, as the electrophile. This is usually done in acidic conditions (concentrated sulfuric acid), so it probably wouldn't work (at least with the example you gave). $\endgroup$ – AS_1000 Feb 26 '18 at 1:13
  • $\begingroup$ Chemists haven't been able to isolate cyanoform as a neat, free acid and only in September 2015, there has been reports of having a successful isolation. So, I don't think cyanoform would be synthesized from general laboratory grade reaction. Its synthesis requires drastic measures and condition. $\endgroup$ – Nilay Ghosh Mar 17 at 5:58

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