338-38-5Relevant articles and documents
Electrochemical syntheses of cyclo[n]pyrrole
Buda, Mihai,Iordache, Adriana,Bucher, Christophe,Moutet, Jean-Claude,Royal, Guy,Saint-Aman, Eric,Sessler, Jonathan L.
, p. 6810 - 6819 (2010)
Cyclo[8]pyrrole was obtained efficiently when 3, 3', 4, 4'-tetraethylbipyrrole was subjected to bulk electrolysis, with yields spanning a range from close to 0% with tetra-n-butylammonium fluoride as the electrolyte, to almost 70% when tetra-n-butylammonium hydrogensulfate was used for this purpose. These observations are consistent with the conclusion that the reaction is controlled by anion-related fac-tors such as a specific templating effect. Note that cyclo[8]pyrrole was the only detectable macrocyclic product obtained from 3, 3', 4, 4'-tetraethylbipyrrole under the conditions of the electrochemical oxidation. When similar electrolyses were performed by using 3, 4-diethylpyrrole as the starting material, two products could be isolated, which were identified as being the cyclo[7]pyrrole and cyclo[8]pyrrole, respectively. Detailed analyses of the oxidized forms of cyclo[7]pyrrole and cyclo[8]pyrrole revealed that under the conditions of the electrolysis these latter species are not stable.