Mechanistic features of S N Ar reactions of neutral and cationic metal-complexed halogenobenzenes with methoxide

A. C. Knipe, Samuel J. McGuinness, W. E. Watts

Journal of the Chemical Society Chemical Communications · 1979 · 21 citations · 0 references

Concepts

Abstract

Rate studies have shown that the activation of halogenobenzenes towards replacement of halide by methoxide in methanol increases through the series of π-attached residues (OC)3Cr < (OC)3Mo < < (η5-C5H5)Fe+ < (OC)3Mn+, with the fluorobenzene complexes more reactive than the chlorobenzene analogues; evidence has been obtained that the cationic complexes readily form ion-pairs with methoxide, resulting in a reduction in their reactivity towards nucleophilic substitution.