Abstract

The relative mobility of the nitro group and fluorine atom in 3,5-dinitro- and 3-fluoro-5-nitrobenzofluorides was estimated by the competing reaction technique using phenols in the presence of potassium carbonate (DMF, 65-95°C). Correlation analysis of the relative rate constants k(NO2)/k(F) and of the differences in the activation parameters (ΔΔH ≠ and ΔΔS ≠) of competing reactions showed the existence of two reaction series for the examined phenols. The higher mobility of the nitro group was found to result from the entropy control of the reactivity of arenes. The mechanism of these reactions is discussed.

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