Abstract
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 ϱ 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.
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