SYNTHESIS AND STRUCTURE OF ASYMMETRIC 2,4,6-TRIAZIDOPYRIDINES
Keywords:azides, pyridines, high-energy materials, nucleophilic substitution, X-ray structural analysis
The reactions of 3-cyanotetrafluoropyridine and tetrachloro-3-trifluoromethylpyridine with sodium azide lead to the corresponding 2,4,6-triazido-5-cyano-3-fluoropyridine and 2,4,6-triazido-5-chloro-3‑trifluoromethylpyridine. With the aid of comparative X-ray structural analysis of 2,4,6-triazido-5‑cyano-3-fluoropyridine and its previously known 3-chloro-substituted derivative it was established that the geometric parameters and reactivity of the azide groups in the asymmetric 2,4,6-triazidopyridines depend not only on the position of these groups in the pyridine ring but also on their mutual orientation in space.
Authors: S. V. Chapyshev, D. V. Korchagin, G. V. Shilov, and S. M. Aldoshin
English Translation in Chemistry of Heterocyclic Compounds, 2011, 47 (7), pp 817-825http://link.springer.com/article/10.1007/s10593-011-0841-x