Articulo
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway
Registro en:
issn:0023-1584
issn:1608-3210
Autor
Allegretti, Patricia Ercilia
Bravo, Rodolfo Daniel
Furlong, Jorge Javier Pedro
Institución
Resumen
Aromatic hydrocarbons are susceptible to direct acylation by benzoic acids with high yields bearing ortho or para alkyl groups as substituents under Friedel–Crafts reaction conditions. The α-H of the alkyl moiety seems to be responsible for the observed relatively high reaction rates of conversion. Carbanion-like species are proposed as reaction intermediates, which also operate as strong bases in the reaction rate-determining steps. Trapping experiments, deuterium isotopic effects, and kinetics data favor a concerted reaction pathway where proton transfer from the hydrocarbon molecule to a carbanionic intermediate takes place with a simultaneous electrophilic attack of the carbonylic carbon atom. Facultad de Ciencias Exactas Laboratorio de Estudio de Compuestos Orgánicos