Aromatic Substitution. 48. Boron Trifluoride Catalyzed Nitration of Aromatics with Silver Nitrate in Acetonitrile Solution

Article abstract of DOI:10.1021/jo00330a032

Benzene, alkylbenzenes, halobenzenes, and anisole were nitrated with silver nitrate/boron trifluoride in acetonitrile solution.Correlation of competitive rates with ?- and ?-complex stabilities indicated that the transition state of highest energy lies relatively early on the reaction coordinate.Data indicate that nitrations occur via a polarized complex of the nitrating agent, with the catalyst undergoing nucleophilic displacement by the aromatic substrate.