Tetrahedron Letters p. 7649 - 7652 (1997)
Update date:2022-08-17
Topics:
White, Emil H.
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.
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