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■ ¹³C NMR Study of Annular Tautomerism of Azoles in the Solid State

Robert Faure, Emile-Jean Vincent, and José Elguero

*Laboratoire de Chimie Organique Physique, Facluté des Sciences et Techniques de Saint Jérôme, Université d’Aix-Marseille III, Avenue Escardille Normandie Niemen (Case 552), 13397 Marseille Cedex 13, France

Abstract

The ¹³C chemical shifts of 1,2,4-triazole, tetrazole, indazole, benzimidazole, and benzotriazole have been obtained from solid samples using the CP-MAS technique. They are discussed in connection with the annular prototropic tautomerism of these azoles and benzazoles. A case of functional tautmerism, that of benzoxazolidin-2-thione, and a case of non-prototropic tautmerism, that of 1-trimethylsilylbenzimidazole, are also studied.