Abstract
A kinetic study of the reaction between substituted styrenes and 4-substituted triazolinediones has been made in solvent benzene at 25°C. The influence of the substituents on the reaction rate has been analyzed. The Hammett correlation with σ gave ϱ values of −0.29 ± 0.02 and −0.61 ± 0.03 for the reaction of parasubstituted styrenes with Me-TAD and Ph-TAD, respectively. The structure-reactivity data support a mechanism for the initial 1:1 adduct formed involving a concerted cycloaddition step with simultaneous bond-making and bond-breaking processes.
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