4-ARYL(BENZYL)SULFONYL-2-CHLORO-5-POLYFLUOROALKYL-1,2,3-TRIAZOLES. THE FIRST MONOCYCLIC N-CHLORO-1,2,3-TRIAZOLES

Abstract

Treatment of  4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4-(p-tolyl-sulfonyl)-2H-[1,2,3]triazole  has  been established by X-ray  structural investigation. The presence of a highly polarized N–Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium  salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5-polyfluoroalkyl-ν-triazoles  in  the  presence of KF gives 4-chloro-5-polyfluoroalkyl-2H-[1,2,3]triazoles.

How to Cite
Bandera, Yu. P.; Kanishchev, O. S.; Timoshenko, V. M.; But, S. A.;
Nesterenko, A. M.; Shermolovich, Yu. G.  Chem. Heterocycl. Compd. 2007, 43, 1138. [Khim. Geterotsikl. Soedin. 2007, 1342.]

For this article in the English edition see DOI 10.1007/s10593-007-0175-x