Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway (original) (raw)

Kinetics and Catalysis, 2002

Abstract

ABSTRACT 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 a-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.

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