The Reactivity-Selectivity Principle and the electrophilic substitution of aromatic compounds

[摘要] 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 sigma(+) for 4-methylbenzyl, benzyl, 4-chlorobenzyl, and 4-nitrobenzyl cations] yielded rho 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. (C) 1997 Elsevier Science Ltd.

[发布日期] 1997-11-03