ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Derivatives of ferrocenes. XIV. Synthesis of new substances by Michael addition starting from chalcones of cinnamoylferrocene type with active reactants

M. Furdík and Š. Toma

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, Komenský University, Bratislava

Abstract:  A basic-catalysed Michael addition was investigated with the respective cinnamoylferrocene, p-chlorocinnamoylferrocene and /5-ferrocenylacryloylbenzene (a „reverse" cinnamoylferrocene) as a substrate and nitromethane, ethyl malonate, ethyl acetoacetate, cyanoacetamide, ethyl cyanoacetate, acetylacetone, cyclopentanone and fluorene, respectively, as a reactant. I t was ascertained that by selection of a convenient method and reaction conditions, positive or good results could be obtained even when other authors [1] reported negative or considerably low yields only. Moreover, an intramolecular aldol cyclization took place when reacting ethyl acetoacetate or cyanoacetamide to form the proper hydroxyderivatives and their anhydrides, eventually the enolates. The structure of these cyclic substances was proved by the analysis of the absorption spectra in both the UY and IR region.

Full paper in Portable Document Format: 201a3.pdf (in Slovak)

Chemical Papers 20 (1) 3–17 (1966)