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-  1978 

Ferrocene Compounds. VII. The Stobbe Condensation of Formylferrocene with Diethyl Glutarate

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Abstract:

Sa?etak The Stobbe condensation of formylferrocene with diethyl glutarate in the presence of potassium tert-butoxide gave (E)-1-ethyl hydrogen 2-ferrocenylmethyleneglutarate (I), which was converted by the action of diazomethane to (E)-1-ethyl 5-methyl 2-ferrocenylmethyleneglutarate (II). The configurations of compounds I and II are assigned through study of their 1H-NMR and IR spectra. This stereochemical assignment is supported by the conversion df compound I to cyclopentadienyl(5,6-dihydro-4-oxo-7-ethoxycarbonylazulenyl) iron (III), which was hydrolized to the corresponding acid (VI). The same acid VI was obtained from half ester I via the corresponding diacid IV and anhydride V. The stereoselectivity of the Stobbe condensation is discussed

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