Aromatic Substitution. 45. Transfer Nitration of Aromatic with N-Nitropyridinium and Quinolinium Ions

Article abstract of DOI:10.1021/ja00530a033

The transfer nitration of aromatics with various N-nitropyridinium and quinolinium salts (PF6^- or BF4^-) was studied.The nitroanions were found to take place via a nicleophilic displacement pathway, involving the N-nitropyridinium ions themselves and not free nitronium ion.Steric factors were, however, shown to play an insignificant role in determining the positional selectivity of nitration.Positional and substrate selectivities were found to be independent of one another and are suggested to be determined in two separate steps.