Abstract
Acylmethylenetriphenylphosphoranes react with aryl azides in refluxing benzene to give 1-aryl-5-substituted-1,2,3-triazoles exclusively. The regiochemistry of the reaction was resolved by comparison of the triazoles with authentic samples, prepared by the Dimroth method. From the kinetic point of view, the reaction is accelerated by electron-withdrawing substituents on the azide and electron-releasing substituents on the ylide. The polarity of the solvent has only a small effect on the reaction rate. Finally, the low entropies of activation support a concerted cycloaddition in the first step of the reaction.
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