About: Synthesis and Electrochemical Reduction of Methyl 3-halo-1-benzothiophene-2-carboxylates     Goto   Sponge   NotDistinct   Permalink

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  • A preparative method for synthesis of the new 3-iodo derivative was elaborated. Electrochemical behaviour of methyl 3-halo-1-benzothiophene-2-carboxylates 1-3 (chloro-, bromo-, iodo-), their reduction and dimer products 4,5 has been investigated at mercury and platinum electrodes using polarography, cyclic voltammetry and RDE methods in non-aqueous dimethylformamide. The reduction in divided cells follows the ECE mechanism, where the primary radical anion is split into halogenide anion and neutral heterocyclic radical, which is immediately reduced by the second electron and protonated. The only reduction product is the HBT (5), whereas the EDim mechanism leading to the dimeric species 4 was not observed at above conditions. Reduction of 1-3 on platinum causes formation of a blocking film on the electrode. Sonication during electrolysis successfully reactivates the electrode.
  • A preparative method for synthesis of the new 3-iodo derivative was elaborated. Electrochemical behaviour of methyl 3-halo-1-benzothiophene-2-carboxylates 1-3 (chloro-, bromo-, iodo-), their reduction and dimer products 4,5 has been investigated at mercury and platinum electrodes using polarography, cyclic voltammetry and RDE methods in non-aqueous dimethylformamide. The reduction in divided cells follows the ECE mechanism, where the primary radical anion is split into halogenide anion and neutral heterocyclic radical, which is immediately reduced by the second electron and protonated. The only reduction product is the HBT (5), whereas the EDim mechanism leading to the dimeric species 4 was not observed at above conditions. Reduction of 1-3 on platinum causes formation of a blocking film on the electrode. Sonication during electrolysis successfully reactivates the electrode. (en)
  • Elektrochemicky byla prostudována redukce 3-halo-1-benzothiofen-2-carboxylátů 1-3 (chloro-, bromo-, jodo-), jejich dimérů a redukčních produktů (4,5) na rtuťových a platinových elektrodách v bezvodém dimethylformamidu pomocí polarografie, cyklické voltametrie a voltametrie na RDE. (Za tímto účelem byla vypracována syntetická metoda pro přípravu nových 3-jodo derivátů.) Redukce látek 1-3 probíhá ECE mechanismem. Na platinových elektrodách se při redukci tvoří film pasivující elektrodu. Sonikace během elektrolýzy účinně odstraňuje blokující vrstvu a reaktivuje elektrodu. (cs)
Title
  • Synthesis and Electrochemical Reduction of Methyl 3-halo-1-benzothiophene-2-carboxylates
  • Syntéza a elektrochemická redukce methyl-3-halo-1-benzothiofen-2-carboxylátů (cs)
  • Synthesis and Electrochemical Reduction of Methyl 3-halo-1-benzothiophene-2-carboxylates (en)
skos:prefLabel
  • Synthesis and Electrochemical Reduction of Methyl 3-halo-1-benzothiophene-2-carboxylates
  • Syntéza a elektrochemická redukce methyl-3-halo-1-benzothiofen-2-carboxylátů (cs)
  • Synthesis and Electrochemical Reduction of Methyl 3-halo-1-benzothiophene-2-carboxylates (en)
skos:notation
  • RIV/61388955:_____/04:00101018!RIV/2005/AV0/A54005/N
http://linked.open.../vavai/riv/strany
  • 242;260
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(GA202/02/0840), P(IAA4040304), Z(AV0Z4040901), Z(MSM 223100001)
http://linked.open...iv/cisloPeriodika
  • 1
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 589327
http://linked.open...ai/riv/idVysledku
  • RIV/61388955:_____/04:00101018
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • halobenzothiophenes; voltammetry; biaryls (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • CZ - Česká republika
http://linked.open...ontrolniKodProRIV
  • [71DE0B742069]
http://linked.open...i/riv/nazevZdroje
  • Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 69
http://linked.open...iv/tvurceVysledku
  • Klíma, Jiří
  • Ludvík, Jiří
  • Svoboda, J.
  • Rejňák, M.
http://linked.open...n/vavai/riv/zamer
issn
  • 0010-0765
number of pages
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