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(Perhalogenmethylthio)heterocyclen. X . Säurekatalysierte Substitutionen an (Perchlorfluormethylthio)pyrrolen und deren agrobiologische Wirkung
Author(s) -
Dorn Silvia,
Eggenberg Peter,
Gerstenberger Michael R. C.,
Haas Alois,
Niemann Ulrich,
Zobrist Peter
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620508
Subject(s) - chemistry , pyrrole , medicinal chemistry , catalysis , salt (chemistry) , tris , stereochemistry , organic chemistry , biochemistry
(Perhalomethylthio)heterocycles. X IX. Mitt.: s. [1]. . Acid‐catalyzed substitutions on (perchlorofluoromethylthio)pyrroles and their agro‐biological activities In the presence of C 4 F 9 SO 3 H the (perhalomethylthio)pyrroles 1a–c react with Cl 3−n F n CSCl (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 CF 3 SCl (catalyst CF 3 SO 3 H) 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 1 H‐ and 19 F‐NMR. spectra are discussed and the agro‐biological properties of the compounds investigated.