Gas-Phase Alkylbenzene Dealkylation

Article abstract of DOI:10.1021/j100448a003

The gas-phase electrophilic attack of radiolytically formed D₃⁺ ions on toluene, ethylbenzene, isopropylbenzene, and tert-butylbenzene was investigated.With the exception of toluene, the analysis of the products showed the formation of benzene for the other alkylbenzenes.The first step of the reaction leads to the formation of an excited arenium ion that, if not collisionally stabilized, can decompose to give benzene and the correspondent alkyl cation.Dialkylarenes are not formed under reaction conditions.The extent of dealkylation, that increases in the order ethylbenzene < isopropylbenzene < tert-butylbenzene, shows a dependence on the substrate concentration.The occurence of competitive reactions is suggested.Comparison with solution chemistry data must take into account the different environmental conditions.