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Synthesis 2000; 2000(3): 357-359
DOI: 10.1055/s-2000-6339
short paper
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Functionalized Cyclopentadienes: Synthesis of 1,3-Bis(1,1-dimethylbut-3-cyclopentadienyl) Systems

Derk Vos* , Peter Jutzi
  • *Fakultät für Chemie, Universität Bielefeld, Universitätsstr. 25, 33615 Bielefeld, Germany; Fax +49 (5 21) 1 06 60 26; E-mail: peter.jutzi@uni-bielefeld.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The synthesis of the new cyclopentadiene C5H4(CMe2CH2CHCH2)2 4 is described. The key step of the reaction sequence is the regioselective formation of the 2-(1,1-dimethylbut-3-enyl)-6,6-dimethylfulvene 2. The substitution pattern of 4 can be confirmed by the structure of the Diels-Alder product obtained from 2 and dimethyl acetylenedicarboxylate. Compound 4 is converted into the corresponding cyclopentadienides 5a, b via metallation with n-BuLi and KH, respectively. Compounds 4 and 5a, b are suitable candidates for the synthesis of functionalized cyclopentadienyl complexes in organometallic chemistry.

alkenyl-substituted cyclopentadienes - fulvenes - NMR spectroscopy - Diels-Alder reaction