期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 23, 页码 6810-6819出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000043
关键词
anions; electrochemistry; electrolysis; oxidative coupling; pyrroles
资金
- National de la Recherche [ANR-09-JCJC-0083-01]
- NSF [CHE-074971]
- Robert A. Welch Foundation [F1018]
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 factors 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]hyrrole, 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.
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