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Topic: nitrobenzene and the Von Richter rearrangement  (Read 7908 times)

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Offline Gregorian

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nitrobenzene and the Von Richter rearrangement
« on: December 30, 2008, 12:34:20 AM »
Hello guys,
I was reading in March's book (2005 edition) at work  ;D  and I saw this reaction called the Von Richter rearrangement.
In this reaction you react a cyanide with a nitrobenzene in ethanol and you get a benzoic acid in the cine position (ortho position of the nitro group) and the nirto group is displaced!
Here is the reaction and mechanism. 
http://en.wikipedia.org/wiki/Von_Richter_reaction

When I was reading though, I thought of the Nucleophilic Aromatic Substitution of pyridine which is highly deactivated. So I thought that since nitrobenzene is deactivated why can't we add -CN to the ortho and para positions without having to displace the NO2 group! I never learned anything about any additions to nitrobenzene, so your answer would be very helpful. 

Thanks :)
in everything God works for the good of those who love him
-Rom 8:28

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