Product distributions
resulting from nitration of polymethylbenzenes in nitric acid-acetic anhydride
mixtures have been determined by gas chromatography. Nitration of a methyl
group occurs in all the substrates studied; such nitration occurs only at a methyl
group para to the methyl most activated to ipso nitration. These results
support the view that side chain nitration occurs through the diene
intermediates which lead to ring acetoxylation.
Reaction of 5-substituted-hemimellitenes (1.2.3-trimethylbenzenes) (3a-c) and 4-substituted-o-xylenes (3d-f) with nitric acid-acetic anhydride gives 4-nitrocyclohexa-2,5-dienones (5a) and (5b) in addition to normal substitution products.
Finally, the rearrangement of the thiosemicarbazone to give the isothiocyanate is the only case to date in which a thioamide or thiourea has undergone the Hofmann reaction.(PH 5-7).
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