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Derivatives of ferrocene. XV. Investigation of the Michael addition to p-substituted cinnamoylferrocene derivatives

M. Furdík and Š. Toma

Komenský University, Bratislava


Abstract:  The Michael addn. reaction of the NCCH2CO2Et on the chalcones of the type Fc-COCH:CHC6H4X-p (Fc = ferrocenyl) was described. If an excess of NCCH2CO2Et is applied, then this reaction is 1st order in the relation to chalcone and the reaction rate is dependent on the substituent. In the correlation log κ vs. Hammett's consts. σ-(p), these values were detd.: ρ = 0.65 ± 0.035 at 60° and ρ = 0.54 ± 0.026 at 50°. The dependence of the reaction rate on temp. is small as indicated from the calcd. activation energy. An increase of 20° increased the reaction rate 2-fold. Comparing the reaction rates of the p-Me2N deriv., p-MeO deriv., and β-ferrocenylacryloylferrocene showed that the Fc radical reaches as much as 60-70% of the electron-donor character of the p-Me2NC6H4 group. The formation of an isomeric chalcone was observed for the β-ferrocenylacryloylferrocene and an isomerization through the addn. product occurred.

Full paper in Portable Document Format: 205a326.pdf (in Slovak)


Chemical Papers 20 (5) 326–335 (1966)

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