Original scientific paper

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

M. Laćan ; Laboratory of Applied Organic Chemistry, Biochemistry Department, Faculty of Technology, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
V. Rapić ; Laboratory of Applied Organic Chemistry, Biochemistry Department, Faculty of Technology, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia

Abstract

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.

Keywords

Hrčak ID:

195952

URI

https://hrcak.srce.hr/195952

Publication date:

22.12.1978.

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