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Int. E d . Engl. 6 , 733 (1967). 78 79 46 [Sec. B. T. L. GILCHRIST AND G. E. GYMER The toluene-p-sulfonamido anion may be lost from this, giving the diazo compound directly, or ring closure (which may be reversible) can take place, giving the triazoline anion (2). I n many of these cases it is impossible to decide, without 15N-labeling experiments, whether the third nitrogen of the triazole ring is derived from the toluene-p-sulfonyl azide or from the activated methylene compound. ^^ Two moles of azide are required, the second being reduced to aniline.

F. 2H-Triazoles from a-Diketone Derivatives . G. Other Routes to 2H-Triazoles . H. 4H-Triazoles . 111. Structure and Physical Properties . A. Structure . B. Spectroscopic Properties . C. Other Physical Properties . IV. Reactions of 1,2,3-Triazoles . A. Electrophilic Substitution . B. Nucleophilic Substitution . C. Migrations of Ring Substituents . D. Transformations of Substituents . E. Removal of Substituents . F. Dimroth Rearrangement . G. Reactions Involving Cleavage of the Triazole Ring H. Salts and Complexes .

E. OYMER [Sec. 11. 1,2,3-triazolesas light stabilizers and as optical brightening agents, and also in their use as precursors for azapurines and similar heterocyclic systems, which are potential carcinostatic agents. The present review, which surveys the literature t o mid-1972, has been restricted to monocyclic 1,2,3-triazoles,since much of the chemistry of benzotriazoles and other fused systems has little in common with monocyclic triazole chemistry. The aim has been to give a broad survey of methods of synthesis and reactions of triazoles; few references are included from before 1960, as these are available from earlier reviews.

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A comprehensive treatise on inorganic and theoretical chemistry vol.VIII N, Cl by Mellor J.W.


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