Ferrocenyl salts as synthons: new ferrocenyl-1,3-diketones

Article abstract of DOI:10.1016/0022-328X(94)24775-E

Reaction of (ferrocenylmethyl)trimethylammonium iodide with the mono-sodium salts of a range of acyclic 1,3-diketones leads smoothly to 2-(ferrocenylmethyl)-1,3-diketones <(C5H5)Fe(C5H4)CH2>CH(COR¹)(COR²), but with the corresponding tetrabutylammonium salts deacylation occurs.With the sodium salt of cyclohexane-1,3-dione, disubstitution occurs to give (2,6-dioxocyclohexane-1,1-diyl)bismethyleneferrocene, <(C5H5)Fe(C5H4CH2)>2C<(CO)2CH2)3>.The lithium salt of acetylferrocene reacts with a range of monocarboxylic esters to provide 1-ferrocenyl-1,3-diketones <(C5H5)Fe(C5H4)>COCH2COR, but simple esters of dicarboxylic acids either do not react, or undergo only monosubstitution. Keywords: Ferrocene; Diketones; Iron