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Synthesis 1996; 1996(1): 71-76
DOI: 10.1055/s-1996-4152
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Rodlike Molecules by Kolbe Electrolysis

G. Nuding, F. Vögtle* , K. Danielmeier, E. Steckhan1
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany, Fax +49(228)735662
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Publikationsdatum:
31. Dezember 2000 (online)

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A new short and simple pathway to rigid, rod-shaped hydrocarbon skeletons, in particular of the oligo-bicyclo[2.2.2]octane type, is described. The key step consists of an electrochemical C-C bond coupling reaction between bridgehead positions of bi- and tricyclic carboxylic acids. Functional groups can be retained, they influence the yield of the C-C bond connection. In this way, otherwise difficult or laborious syntheses are shortened, and rigid, non-collapsable nano size spacer units are easily available. The optimized electrochemical procedures are described in detail.

Kolbe electrolysis - monoesters of dicarboxylic acids - rodlike molecules - repetitive synthesis - oligo-bicyclo[2.2.2]octane