1,1-Diferrocenylethane. A Friedel-Crafts Rearrangement

Electro‐ and Magnetocommunication in [5,5]Ditrovacenyls, [(η7‐C7H7)V(η5‐C5H4‐X‐η5‐C5H4)V(η7‐C7H7)], Mediated by the Spacers X=(Z)CHCH, (E)CHCH, >CCH2, CH2CH2, and CH2

“…However, the low-yield access to the latter ketone [13] disfavored this approach and, instead, the path involving dehydration of the tertiary carbinol 10CC was followed. This synthesis has precedent in the preparation of vinylferrocene from acetylferrocene and LiAlH 4 [14] and of 1,1-diferrocenylethene from diferrocenylketone and CH 3 MgBr; [15] in both cases dehydration of the respective ferrocenylcarbinol forms the terminal step.…”

Ring Substitutions and Secondary Reaktions of Aromatic‐Metal π‐Complexes, Part I

“…In the reaction of 1,2-dichloroerhane with ferrocene in the presence of aluminum chloride, Nesrneyanov and Kochetkova [5,8] obtained diferrocenylethane along with a high polymer material (Section 16), and by multiple interlinking of two ferrocene molecules, pentaethylenediferrocene and dodecaethylenetetraferrocene. Later, Rinehurt [9] proved that the "diferrocenylethane" was really the unsymmetrical rearrangement product, 1, I-diferrocenylethane. In a normal course of reaction, 1,2-diferrocenylethane would be expected.…”

“…Besides the synthesis of bis(tetrahydr0inde-ny1)iron from bis(indeny1)iron mentioned above [3 11, tricarbonyl(dihydropentaleny1)manganese can similarly be converted to tricarbonyl(tetrahydropentaleny1)manganese with hydrogen and Runey nickel [33,34]. Likewise, the ferrocene derivatives cyclopentylferrocene [16], unsym.-di(ferroceny1)ethane [9], 1 -dimethylaminoethyl-2ethylferrocene, 2-cyano-1 -ethylferrocene and 1 -hydroxymethyl-2-ethylferrocene [36] have been made available by catalytic hydrogenation of the corresponding alkenyl compounds. The reaction products are deeply colored, crystalline, and usually stable in air.…”

“…arated in the case of 1 ,l'-di-a-hydroxyisobutylferrocene [60]. a,a-Diferrocenylethanol was obtained by the reaction of methylmagnesium iodide with diferrocenylketone [9].…”

gem-Diferrocenylalkane derivatives. Acid-catalyzed condensation of ferrocene with methyl levulinate and 5-hydroxy-2-pentanone

“…1,1 -Diferrocenylethane is formed by reaction of ferrocene with 1,2-dichloroethane (aluminum chloride catalyst). 12 A study was made of the condensation of ferrocene with levulinic acid and methyl levulinate employing polyphosphoric, phosphoric, sulfuric, and trifluoroacetic acid catalysts. Slow addition of an excess of methyl levulinate to ferrocene and polyphosphoric acid at temperatures below 80°f avors a high conversion of ferrocene to methyl 4,4-diferrocenylpentanoate (3, 40% conversion, 67% yield based on reacted ferrocene).…”