Can we predict reactivity for aromatic nucleophilic substitution with [18F]fluoride ion?

CAN WE PREDICT REACTIVITY FOR AROMATIC NUCLEOPHILIC SUBSTITUTION WITH (1sFJFLUORIDE ION?

The correlation between the 1%-NMR chemical shift of the aromatic ring carbon bearing the leaving group and the yield of nucleophilic aromatic displacement with no-carrier-added [ 18Flfluoride ion was evaluated. In comparison of structurally analogous compounds (fluoro, nitro and trimethylammonium substituted benzaldehydes, benzophenones and benzonitriles), the 13C-NMR chemical shift of the rea...

Modern Nucleophilic Aromatic Substitution

Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides

A computational approach using density functional theory to compute the energies of the possible σ-complex reaction intermediates, the "σ-complex approach", has been shown to be very useful in predicting regioselectivity, in electrophilic as well as nucleophilic aromatic substitution. In this article we give a short overview of the background for these investigations and the general requirement...

Synthesis of polynitroxides based on nucleophilic aromatic substitution.

The scope and limitations of the synthesis of polynitroxides by nucleophilic substitution of electron-deficient fluorinated aromatic compounds are described. The method provides a facile route to the formation of polynitroxides exhibiting strong electron exchange between nitroxide groups.

Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 ...