(PERHALOMETHYLTHIO)HETEROCYCLES .10. ACID-CATALYZED SUBSTITUTIONS ON "(PERCHLOROFLUOROMETHYLTHIO)PYRROLES AND THEIR AGRO-BIOLOGICAL ACTIVITIES

被引：22

作者：

DORN, S ^{[1
]}

EGGENBERG, P ^{[1
]}

GERSTENBERGER, MRC ^{[1
]}

HAAS, A ^{[1
]}

NIEMANN, U ^{[1
]}

ZOBRIST, P ^{[1
]}

机构：

[1] RUHR UNIV BOCHUM,LEHRSTUHL ANORGAN CHEM 2,D-4630 BOCHUM,FED REP GER

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 05期

关键词：

D O I：

10.1002/hlca.19790620508

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Perhalomethylthio)heterocycles. X . 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. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1442 / 1450

页数：9

共 9 条

[1]

[Anonymous], 1972, ANGEW CHEM, V84, P294

[2]

CIAMICIAN GL, 1883, BER, V16, P2388

[3]

Effenberger F., 1972, ANGEW CHEM, V84, P295

[4]

EFFENBERGER F, 1973, Patent No. 2139944

[5] DETERMINATION OF DISSOCIATION-CONSTANTS OF HJ, FSO3H AND CF3SO3H IN GLACIAL ACETIC-ACID [J].

ENGELBRECHT, A ;

RODE, BM .

MONATSHEFTE FUR CHEMIE, 1972, 103 (05) :1315-+

[6] Metallic salts of pyrrol, indol and carbazol [J].

Franklin, EC .

JOURNAL OF PHYSICAL CHEMISTRY, 1920, 24 (02) :81-99

[7] PERHALOGENMETHYLMERCAPTO-HETEROCYCLEN, .9. (PERCHLORMETHYLMERCAPTO)PYRIDINE AND (PERFLUORMETHYLMERCAPTO)PYRIDINE [J].

HAAS, A ;

NIEMANN, U .

JOURNAL OF FLUORINE CHEMISTRY, 1978, 11 (05) :509-518

[8] (PERHALOMETHYLTHIO)HETEROCYCLES .8. (PERCHLOROFLUOROMETHYLTHIO)- AND (HALOFORMYLTHIO)-N-HETEROAROMATICS [J].

HAAS, A ;

NIEMANN, U .

CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (01) :67-77

[9] NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY - PROTON SPECTRA OF DIALLYLMERCURY [J].

ZIEGER, HE ;

ROBERTS, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) :2826-&

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