The kinetics of quaternization of a number of 2-substituted benzothiazoles with alkyl iodides and phenacyl bromide have been studied in nitrobenzene. The order of reactivity of different substituted benzothiazoles has been found to be -H > NO2 > Cl. The relative reactivity of 2-amino and 2-methyl derivatives has been ascribed to a solvation phenomenon. The analysis of rho values from the Hammett equation suggests two possible routes for the transmission of electron density.
Volume 134, 2022
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