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The derivatives of ferrocene. V. Aldol condensation of 1,1'-diacetylferrocene with alilohatic aldehydes

M. Furdík, Š. Toma, and J. Suchý

Komensky University, Bratislava

Abstract: cf. CA 55, 18692e; 56, 7355a. The aldol condensation of 1,1'-diacetylferrocene with aliohatic aldehydes and consequent cyclization with intramol. Michael addn. was described. This reaction is similar to that of the basic catalyzed condensation of BzH and its derivs. with 1,1'-diacetylferrocene and 1-acetyl-1'-acylferrocene out the yield is very much lower, from 9 to 18%. With HCHO, 1,1'-(α,α'-dioxopentamethylene)ferrocene, yellow crystals, m. 253°, was formed; with AcH, 1,1'-(α,α'-dioxo-γ-methylpentamethylene)ferrocene, yellow needle crystals, m. 251.5-53°; with propionaldehyde, 1,1'-(α,α'-dioxo-γ-ethylpentamethylene)ferrocene, yellow crystals, m. 214.5-16.5°; with butyraldehyde, 1,1'-[α,α'-dioxo-γ-propylpentamethylene]ferrocene, yellow crystals, m. 239-40°; with isobutyraldehyde, 1,1'-(α,α'-dioxo-γ-isopropylpentamethylene)ferrocene, yellow crystals, m. 269.5°, and with isovaleraldehyde, 1,1'-(α,α'-dioxo-γ-isobutylpentamethylene)ferrocene.

Full paper in Portable Document Format: 166a449.pdf (in Slovak)

Chemical Papers 16 (6) 449–457 (1962)