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Synlett 1994; 1994(8): 653-654
DOI: 10.1055/s-1994-22963
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Zirconocene Complexes of [2.2]Paracyclophanes with Formal Triple Bonds in the Bridges

Burkhard König* , Martin A. Bennett, Armin de Meijere
  • *Research School of Chemistry, The Australian National University, GPO Box 4, Canberra ACT 2601, Australia and Institute für Organische Chemie der Technischen Universitauml;t Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
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Publication Date:
18 September 2002 (online)

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Zirconocene complexes of [2.2]paracylophanes with formal triple bonds in the bridges, corresponding to zirconacyclo-propenes, were synthesized from [2.2]paracylophan-1-ene (1) and 1,9(10)-dibromo[2.2]paracyclophan-1,9-diene (5) via their vinyl lithium derivatives and characterized by spectroscopic methods. The zirconocene-alkyne complexes 7, 9 react with bromine or iodine with loss of the bis(cyclopentadienyl)zirconium moiety to yield the expected stable halogenated products 8 and 10, respectively. Insertion of 2-butyne into the initially formed 16e complexes gave zirconacyclopentadiene complexes 3, 9.