Collect. Czech. Chem. Commun. 1987, 52, 166-173

Study of the reactivity of 2-(3-chlorobenzylidene)[3]ferrocenophane-1,3-dione

Viera Kaliská, Marta Sališová, Eva Solčániová and Štefan Toma

Department of Organic Chemistry, Comenius University, 842 15 Bratislava


The addition of different C-nucleophiles to 2-(3-chlorobenzylidene)[3]ferrocenophane-1,3-dione has been studied. In most cases, the addition has led to expansion of the strained 3-membered bridge to the 7-membered one. An analogous bridge expansion has been observed also in the reaction of 2-(4-chlorobenzylidene)[3]ferrocenophane-1,3-dione with 1,3-cyclohexanedione. 2-(3-chlorobenzylidene)[3]ferrocenophane-1,3-dione reacts with vinyl ethyl ether as a heterodiene, yielding the 4 + 2 cycloadduct.