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Synlett 1991; 1991(5): 324-326
DOI: 10.1055/s-1991-34735
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Highly Substituted Cyclopentadienes from [β-Dimethylaminovinylcarbene] chromium Complexes and Alkynes

Michael Duetsch* , Rolf Lackmann, Frank Stein, Armin de Meijere
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, D-3400 Göttingen, Germany
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Publication Date:
07 March 2002 (online)

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Cycloadditions of pentacarbonyl[(2-cyclopropyl-2-dimethylaminoethenyl)ethoxycarbene]chromium complexes 3a, prepared from pentacarbonyl [(2-cyclopropylethynyl)ethoxycarbene]chromium complexes and dimethylamine, react with alkynes to give good yields of 1-propyl- or 1-phenyl-substituted 5-cyclopropyl-5-dimethylamino-3-ethoxycyclopentadienes (6a-R′). Yields are drastically lower with any substituent other than cyclopropyl in the starting material, but are somewhat improved by formation of the chelated tetracarbonyl complexes 4 prior to cycloaddition.