title: Dicationic intermediates involving protonated amides: dual modes of reactivity including the acylation of arenes.
abstract: In the Brønsted superacid CF(3)SO(3)H (triflic acid), amides are able to form reactive, dicationic electrophiles. It is shown that these dicationic intermediates participate in two distinctly different types of electrophilic reactions. The protonated amide increases the reactivity of an adjacent electrophilic group, and the protonated amide group itself shows enhanced reactivity arising from an adjacent cationic charge. In the latter case, several types of amides are even capable of reacting with benzene by Friedel-Crafts acylation. [reaction--see text]
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA. dklumpp@niu.edu
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
authors.forename: Rendy
authors.initials: R
authors.lastname: Rendy
authors.forename: Yun
authors.initials: Y
authors.lastname: Zhang
authors.forename: Alma
authors.initials: A
authors.lastname: Gomez
authors.forename: Aaron
authors.initials: A
authors.lastname: McElrea
mesh_terms: D000215:Acylation; D000577:Amides / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D011522:Protons; D013696:Temperature
chemical_list: D000577:Amides; D002412:Cations; D011522:Protons