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Synlett 1996; 1996(6): 542-544
DOI: 10.1055/s-1996-5468
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Unexpected Pd-Catalysed Substitution on the Triquinanedione System - An Approach to centro-Substituted Triquinanes

Richard Zuber, Gunter Carlens, Rainer Haag, Armin de Meijere*
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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Centrally aryl- and alkenyl-substituted tricyclo[5.2.1.04,10]dec-8-ene-3,5-diones 7 can be prepared by palladium-catalysed coupling of triquinenedione with aryl and alkenyl iodides, respectively. A mechanistic rationalisation based on the results for various conditions and other model compounds is presented. Applying this new reaction as a key step, centro-phenyltriquinacene 19 and methyl triquinanedione-centro-carboxylate 20 were prepared in four-step sequences each.

C-C bond formation - palladium catalysis - triquinanes - centro-substituted - triquinacene - centro-substituted