In 70–77% sulphuric acid, the nitration of NN-dimethyl-p-toluidine proceeds in two clearly separated stages: the formation of the σ-complex (I) by ipso-attack and the slow rearrangement of this ion to the nitrocompound (II).
K. Fujiwara, J. C. Giffney and J. H. Ridd, J. Chem. Soc., Chem. Commun., 1977, 301 DOI: 10.1039/C39770000301
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