The reactivity-selectivity principle and the electrophilic substitution of aromatic compounds

Article abstract of DOI:10.1016/S0040-4039(97)10083-1

The application of the Reactivity-Selectivity principle (RSP) to the Friedel-Crafts alkylation reaction has been reinvestigated using the N- nitrosoamide decomposition as the source of electrophiles. Plots of p(f) vs σ⁺ for 4-methylbenzyl, benzyl, 4-chlorobenzyl, and 4-nitrobenzyl cations] yielded p values of -3.4, -2.5, -2.4, and -1.2, resp. The data indicate that the Reactivity-Selectivity Principle is applicable to the electrophilic substitution of aromatic compounds contrary to a claim in the literature. A claim that a reactivity reversal should occur in Friedel-Crafts benzylation is also shown to be in question.