Friedel-Crafts acylations of ferrocene i...
Highly effective asymmetric hydrogenatio...
A series of mono- and 1,1'-diheteroatom-...
An efficient and flexible asymmetric syn...
The synthesis of a C2 symmetric 1,1′ ,2,...
ferrocene
benzoyl chloride
1,1’-dibenzoylferrocene
Conditions | Yield |
---|---|
With aluminium chloride; In dichloromethane; ferrocene (1.0 equiv.) added to a stirred suspension of benzoyl chloride(2.2 equiv.) and aluminium chloride (2.2 equiv.) in dichloromethane, st irred at room temp. overnight (16 h); washed with water, organic layer passed through a plug of alumina, washed with chloroform, washings concentrated in vacuo, crude product purified by flash column chromy. on silica gel (TLC Rf 0.26 (1:1 ether-hexane)), elem. anal.;
|
99% |
With aluminium trichloride; In dichloromethane; to suspn. of AlCl3 in CH2Cl2 ligand was added, soln. of Fe-complex in CH2Cl2 was added, stirred for 3 ds at room temp. under Ar; aq. soln. of NaHCO3 was added, extd. with CH2Cl2, washed with aq. NaHCO3, dried over MgSO4, concd. under reduced pressure, column chromy. on silica gel with pentane-Et2O; elem. anal.;
|
87% |
With aluminium trichloride; benzoyl chloride; In dichloromethane; soln. of C6H5COCl and AlCl3 in dry CH2Cl2 was added dropwise over a period of 1 h to a stirred soln. of ferrocene in dry CH2Cl2; soln. was refluxed for 30 min, hydrolized with 0.1 M HCl, product worked up; solid chromd. on alumina using benzene, following by ether ewluant;
|
86% |
With aluminum (III) chloride; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
|
75% |
With AlCl3; In dichloromethane;
|
ferrocene
benzoyl chloride
benzoylferrocene
1,1’-dibenzoylferrocene
Conditions | Yield |
---|---|
With 1-ethyl-3-methylimidazolium iodide-AlCl3; (argon); very slow addn. of AlCl3 to 1-ethyl-3-methylimidazolium iodide, addn. of ferrocene to the ionic liquid, stirring (10 min), ice bath (0°C), addn. of BzCl, stirring (0°C, 2 h), quenching (2 M HCl); extraction (CH2Cl2), drying (MgSO4), concn. (vac.), column chromy. (SiO2, hexanes/ethyl acetate, 10:1 to 1:1);
|
83% 12% |
With 1-ethyl-3-methylimidazolium iodide-AlCl3; (argon); very slow addn. of AlCl3 to 1-ethyl-3-methylimidazolium iodide, addn. of ferrocene to the ionic liquid, stirring (10 min), ice bath (0°C), addn. of BzCl, stirring (0°C, 2 h), quenching (2 M HCl); extraction (CH2Cl2), drying (MgSO4), concn. (vac.), column chromy. (SiO2, hexanes/ethyl acetate, 10:1 to 1:1);
|
12% 83% |
ferrocene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at 20 ℃; Inert atmosphere;
benzoyl chloride; In tetrahydrofuran; dichloromethane; at -78 - 20 ℃; for 2.5h; Inert atmosphere;
|
65% 16% |
ferrocene
phthalic anhydride
benzoyl chloride
(C5H4COC6H5)Fe(CH3OH)3(1+)
ferrocene-1,1' diylbis(diphenylmethanol)
Fe(C5H4C(OH)(C6H5)CCC(CH3)2OOC(CH3)2CH2CH2CH3)2
1,1'-bis[(3-methylphenylimino)phenylmethyl]ferrocene