(Perhalomethylthio)heterocycles. X
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Acid‐catalyzed substitutions on (perchlorofluoromethylthio)pyrroles and their agro‐biological activities
In the presence of C4F9SO3H the (perhalomethylthio)pyrroles 1a–c react with Cl3−nFnCSCl (n = 1–3) to give mixtures of the 2,5‐ and 2,4‐disubstituted pyrroles 2a–f and 3a–h. 2a and 3a react with CF3SCl (catalyst CF3SO3H) yielding 2,3,5‐tris (trifloromethylthio)pyrrole (4a), which under similar conditions reacts further to give 2,3,4,5‐tetrakis (trifluoromethylthio)pyrrole (5). As a by‐product during the conversion of 3a to 4a 2,3,4‐tris (trifluoromethylthio)pyrrole (4b) is formed. The pyrroles 2a, 4a and 5 form the mercury salts 6a–c; compound 5 yields also a silver salt 7. The 1H‐ and 19F‐NMR. spectra are discussed and the agro‐biological properties of the compounds investigated.
In Gegenwart von Perfluorbutylsulfonat (C4F9SO3H) reagieren die Pyrrole (I) mit den entsprechenden (II) zu Gemischen aus den disubstituierten Pyrrolen (III) und (IV).
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