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Derivatives of ferrocene. II. The formation of heterocyclic compounds from diacetylferrocene

M. Furdík, Š. Toma, J. Suchý, and P. Elečko

Komensky University, Bratislava

Abstract: cf. CA 55, 16508d. The reaction of diacetylferrocene (I) with aromatic aldehydes in MeOH and catalyzed by NaOH was studied. I with benzaldehyde, piperonal, o-chlorobenzaldehyde, furfural, and m-nitrobenzaldehyde underwent aldol condensation with one of the Ac groups of I and an intramol. Michael addn. reaction (partially with m-nitrobenzaldehyde) with the formation of a heterocyclic ring (8 members including Fe). These compds. were isolated: 1,1'-(α,α'-dioxo-γ-phenylpentamethylene)-ferrocene, orange-yellow, m. 300°; 1,1'-[α,α'-dioxo-γ-(3,4-methylenedioxyphenyl)pentamethylene]ferrocene, orange-yellow needles, decompg. at 295°; 1,1'-[α,α'-dioxo-γ-(o-chlorophenyl)pentamethylene]ferrocene, yellow scales, m. 267-9°; 1,1'-[α,α'-dioxo-γ-(α-furyl)pentamethylene]ferrocene, yellow, m. 264-5°; 1,1'-[α,α'-dioxo-γ-(m-nitrophenyl)pentamethylene]ferrocene, yellow needles, decompg. at 290°. With o-, m-, and p-nitrobenzaldehydes only aldol condensation occurred (except with m-O₂NC₆H₄CHO when a partial Michael reaction) and these compds. were isolated: 1-acetyl-1'-(o-nitrocinnamoyl)ferrocene, oil; 1-acetyl-1'-(m-nitrocinnamoyl)ferrocene, red-brown, m. 200-2°; 1-acetyl-1'-(p-nitrocinnamoyl)ferrocene, red needles decompg. at 265°. Infrared spectrum were given.

Full paper in Portable Document Format: 151a45.pdf (in Slovak)

Chemical Papers 15 (1) 45–62 (1961)