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• W2077697783 abstract "Um die Hypothese des intermediären Auftretens von Brom und Dipyrrylmethan bei der Bildung von Dipyrrylmethinen aus α-Brom- und α-Brommethylpyrrolen überprüfen zu können, sind die Kinetik der Umsetzung des 5-Äthoxycarbonyl-3-äthyl-2-brommethyl-4-methylpyrrols mit dem 5-Äthoxycarbonyl-3-äthyl-2-brom-4-methylpyrrol in Chloroform sowie diejenige der Bromoxidation der angenommenen Zwischenstufe 5,5′-Diäthoxycarbonyl- 3,3′-diathyl-4,4′-dimethyl-2,2′-dipyrrylmethan in Tetrachlorkohlenstoff untersucht worden. Obwohl das Ergebnis dieser Untersuchung nicht der voranstehenden Annahme widerspricht, stehen alle anderen Beobachtungen stark dagegen. Besonders schwerwiegend ist, daß aus α-Jodmethyl und α Jodpyrrolen, trotz der Unfähigkeit des Jods Dipyrrylmethane zu Dipyrryl- methinen zu oxidieren, ebenfalls Dipyrrylmethine entstehen. - Es wird ein anderer Additions- und Eliminierungsmechanismus vorgeschlagen und über die Selbstumwandlungsprodukte des 5,5′-Diäthoxycarbonyl-3,3′-diäthyl-4,4′-dimethyl-2,2′-dipyrrylmethin-dibrombromids berichtet. Electrophilic Heteroaromatic Substitutions; Formation of Dipyrrylmethines from α-Bromo- and α-Bromomethylpyrroles in Aprotic Solvents In order to test the hypothesis of the intermediacy of bromine and dipyrrylmethane in the reaction of an α-bromopyrrole with an α-bromomethylpyrrole, which leads to the formation of dipyrrylmethines, a kinetic study was performed on the reaction of 5-ethoxycarbonyl-3- ethyl-2-bromomethyl-4-methylpyrrole with 5-ethoxycarbonyl-3-ethyl-2-bromo-4-methyl- pyrrole in chloroform and on the bromine oxidation of the supposed intermediate 5,5′-di- ethaxycarbonyl-3,3′-diethyl-4,4′-dimethyl-2,2′-dipyrrylmethane in carbon tetrachloride. Although the preceding hypothesis cannot be rejected on the basis of the results of the kinetic study, the bulk of the other experimental evidence strongly disfavours it. Such opposing evidence is provided, in particular, by the formation of a dipyrrylmethine from an α-iodo- and an α-iodomethylpyrrole despite the ascertained inability of iodine to oxidize dipyrryl- methanes to dipyrrylmethines. An alternative addition-elimination mechanism is proposed. In addition, a detailed report on the self-transformation products of 5,5′-diethoxycarbony1- 3,3′-diethyl-4,4′-dimethyl-2,2′-dipyrrylmethine dibromobromide is given." @default.
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• W2077697783 date "1975-10-21" @default.
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• W2077697783 title "Elektrophile heteroaromatische Substitutionen; Bildung von Dipyrrylmethinen aus α-Brom- und α-Brommethylpyrrolen in aprotischen Lösungsmitteln" @default.
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• W2077697783 doi "https://doi.org/10.1002/jlac.197519750915" @default.
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