Collect. Czech. Chem. Commun. 1987, 52, 174-181

Michael additions to metallocene analogues of chalcones

Jozef Federič and Štefan Toma

Department of Organic Chemistry, Faculty of Sciences, Comenius University, 842 15 Bratislava


Eleven analogues of chalcones were synthesized; the variously substituted ferrocenyl, ruthenocenyl or η5-cyclopentadienyltricarbonylmanganese are attached to the β-carbon of the chalcone double bond. Methyl malonate was added to eight selected chalcones. The effect of an aryl group on the chemical shift difference of diastereotopic -COOCH3 groups is discussed. The Vilsmeier-Haack formylation was employed to prepare 1'-chloro and 1'-bromoferrocenecarbaldehydes. The synthesis of 2-chloroferrocenecarbaldehyde from 2-chloroferrocenylmethyldimethylamine is also described.