Gas-phase reaction of benzoyl cation with arenes. High selectivity of a gaseous, charged electrophile

Abstract

Gaseous benzoyl cations have been obtained from the reaction of CO with Ph⁺ ions formed by the β-decay of multitritiated benzene; the benzoyl ions display high selectivity in their gas-phase reaction with ambident aromatic substrates, e.g. phenol and aniline, with a marked bias in favour of the n-type nucleophilic centres and do not react appreciably with the π-system, even if it is strongly activated in the case of pentamethylbenzene.