Collect. Czech. Chem. Commun. 1982, 47, 2246-2257

Kinetic study of cyclization of 1-acyl-1'-alkenoylferrocenes. The effect of substitution on the donor and acceptor of Michael addition upon activation parameters of the reaction

Štefan Tomaa and Anton Gáplovskýb

a Department of Organic Chemistry
b Institute of Chemistry, Comenius University, 842 15 Bratislava


Two series of disubstituted ferrocenes, 1-acyl-1'-cinnamoylferrocenes and 1-acyl-1'-alkenoylferrocenes, were prepared and kinetics of their cyclization to [5]ferrocenophane-1,5-dione derivatives has been studied. It was found that substitution on the double bond of the acceptor affects the activation parameters of the reaction less than substitution on the donor of Michael addition. Bulky substituents increase markedly ΔH##f up to 116 kJ mol-1 and ΔS##f up to +44 J mol-1 K-1.