Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway
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....
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| Autores principales: | , , |
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| Formato: | Articulo |
| Lenguaje: | Inglés |
| Publicado: |
2002
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| Materias: | |
| Acceso en línea: | http://sedici.unlp.edu.ar/handle/10915/132695 |
| Aporte de: |
| Sumario: | 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. |
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