ChemInform Abstract: Arylferrocenyl‐1,3‐butadienes.

Abstract

Starting with the α,β‐unsaturated ketones (I), the title compounds (V) are prepared via the carbinols (III) and characterized as the adducts (VII) with maleic anhydride (VI).

Fragmentation and 1,2-Addition Reactions upon Action of Methyllithium on Coupling Products of Ferrocenecarbaldehyde with Dibenzoylmethane

“…The mechanism of cationic cycloaddition to ferrocenylbuta-1,3-dienes and the effect of stereoelectronic factors have been studied in detail earlier. [9] It is noteworthy that cyclodimer 8 is formed as a single diastereomeric ( 1 H NMR data) despite the presence of three stereogenic centers. The physicochemical characteristics of compound 8 and 1 H NMR spectroscopic data totally coincide with those reported earlier.…”

“…The physicochemical characteristics of compound 8 and 1 H NMR spectroscopic data totally coincide with those reported earlier. [9] Compounds 9 and 10 resulted from the classical 1,2-addition of methyllithium to the carbonyl group followed by dehydration of tertiary alcohols 16 and 17 in an acidic medium (Scheme 6).…”

“…To this end, the reactions of these compounds with methyllithium have been investigated. (3) was made to react with excess of methyllithium; the reaction mixture was quenched with water and concentrated, and the residue was treated with glacial acetic acid to give compounds (6)(7)(8)(9)(10)(11) isolated by column chromatography on alumina (Scheme 4).…”

3,5-Bis(ferrocenylmethylene)-1-methyl-4-methylenepiperidine. Synthesis and some chemical properties

“…The mixtt, re was stirred at 20 ~ for 4 h. and 200 mL of water was added, l'he reaction products were extracted with benzene (3x50 mL). After the solvent had been evaporated it7 racuo, the residue was ehromatographed on AI20 ~ iusing benzene as the elnent) to give 0.22 g il I%) of 3,5-bisiferrocenylmethylene)-l-methyl-4-methylenepiperidine (3) Ferrocenylmethylene-3-( ferrocenylmethan-l-ylium-I-yl)-i,4-dimethyl-1,2,5,6-tetrahydropyridinium bis(tetrafluoroborate) ( Thermal cyclodimerization of triene 3. A solution of triene 3 {0.5 g. I mmot) in 50 mL of m-xylene was refluxcd for 4 h. After evaporation of the solvent in vacuo, the residue ,,,,as chromatographed on AI20 ) (using benzene as the eluem) to give (I.22 g (43%) of 8-ferrocenyl-4,3",5"-tris(ferrocenylmethy ene)-2 I "-dimeThvlspiro I 1, 2,3,4,5,6,7.8- …”

“…we found that diferrocenyltriene ..I is [brmed in a low yield even during the standard dehydration, of alcohol 5 on treatment with POCI:; in pyridine. 3 The major product formed in tile reaction was spiro cyclodimer ~6). …”