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Synthesis 1995; 1995(1): 33-35
DOI: 10.1055/s-1995-3849
short paper
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Double Introduction of (η 4-2,4-Pentadienoyl)Fe(CO)3 Groups into Cyclopentadienes

Saburo Nakanishi* , Katsuhisa Kumeta, Kenji Terada
  • *Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture, 1-1 Gakuen-cho, Sakai, Osaka J-593, Japan
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Publication Date:
31 December 2000 (online)

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Reaction of carboxylic acid chlorides adjacent to (η 4-diene)Fe(CO)3 fragments with cyclopentadienyllithium resulted in double introduction of (η 4-2,4-pentadienoyl)Fe(CO)3 groups at vicinal carbons of cyclopentadiene rings. The diiron complexes thus obtained are a mixture of two diastereomers in 1:1 ratio with respect to the chiral (η 4-diene)Fe(CO)3 fragments. The structure of the diiron complex was confirmed by X-ray crystal analysis. Oxidation of the diiron complexes with ceric ammonium nitrate gave 1-(5’-substituted-2’,4’-pentadienoyl)-6-hydroxy-6-(4’-substituted-1,3’-butadienyl)fulvenes in good yields.

η 4-dienetricarbonyliron - 1,2-difunctionalization - fulvenes - diastereoisomers - cyclopentadienyl anion

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