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DOI: 10.1055/s-2001-12769
Methylated Dihydropentafulvalenes and Pentafulvalenides from Tetramethylcyclopentadiene Derivatives
Publication History
Publication Date:
28 September 2004 (online)
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Abstract
Treatment of tetramethylcyclopentadienyllithium (1Li) with CuCl2 or bromotetramethylcyclopentadiene (4), respectively, as well as reaction of stannylated tetramethylcyclopentadiene with 4 in presence of PdBr2 gave two isomeric octamethyldihydropentafulvalenes (3 and 5), of which 5 was deprotonated to a highly substituted cyclopentadienyl anion. Conversion of 1Li to iodotetramethylcyclopentadiene (7) and reaction of 7 with cyclopentadienyl anion yielded three tautomers of tetramethyldihydropentafulvalene (8a, 8b,and 8c) or exclusively 8a depending on the conditions. The crystal structures of 3 and 8a have been determined, and the isomers of 8 have been converted into the corresponding dianion.
Key words
dihydropentafulvalenes - bicyclopentadiendiyl dianion - coupling - cyclopentadienes - lithiation
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References
Further data may be obtained on request from The Director, Cambridge Crystallographic Data Centre, Lensfield Road, Cambridge CB2 1EW, UK by quoting the number CCDC 149911.
23Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen, Germany by quoting the number CSD 405749.