I wonder why Chemplayer’s procedure should produce selectively o-nitrotoluene, because I could find no publication that says so. The paper that
Chemplayer refers to only demonstrates that it is possible to nitrate aromatics with the Nitrate/H2SO4/DCM-Method. Toluene was not even among the
compounds that were tested by the authors. And the other compounds in the paper were not nitrated very selectively.
In Mellor, JM, et al., Tetrahedron 2001 it is reported that nitrating toluene with metal nitrate /sulfuric acid systems in DCM produces a similar
isomeric ratio as the conventional mixed acid nitration.
Therefor I wonder if there is any publication that demonstrates that the nitration of toluene in DCM is indeed regioselective.
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