1271-15-4

Upstream product

• 102-54-5 ferrocene 
• 109-72-8 n-butyllithium 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 1273-76-3 iodoferrocene 
• 12145-93-6 1,1'-diiodoferrocene 
• 1293-65-8 1,1'-dibromoferrocene 
• 1273-73-0 bromoferrocene 
• 1273-74-1 chloroferrocene 
• 594-19-4 tert.-butyl lithium 
• 811-49-4 ethyllithium 
• 591-51-5 phenyllithium 
• 1274-09-5 bis(ferrocenyl)mercury 
• 598-30-1 sec.-butyllithium 

Downstream Products

• 102-54-5 ferrocene 
• 11105-90-1 bis(μ-fulvalenediyl)diiron 
• 114467-16-2 (OEP)Ge(C₆H₅)(Fc) 
• 1272-44-2 benzoylferrocene 
• 12098-17-8 (diphenylphosphin)ferrocene 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 

Relevant academic research and scientific papers

Polar cofacially fixed sandwich complexes: Do they demonstrate second harmonic generation (SHG)?

For the purpose of possible second harmonic generation (SHG) a cationic and a neutral sandwich unit were cofacially arranged in a three-step synthesis starting from 1,8-diiodonaphthalene. First, 1-cyclopentadienyl-8-iodonaphthalene (2) was formed, then the neutral ferrocenyl substituent was fixed in the 8-position by a Negishi cross-coupling reaction. The deprotonation of the cyclopentadienyl substituent, and the subsequent coordination of the half-sandwich fragments ML = [Fe(η5-C5Me 5)]+, [Rh(η5-C5Me 5)]2+, [Ir(η5-C5Me 5)]2+, [Ru(η6-C6H 6)]2+ to the cyclopentadienyl anion revealed the desired dinuclear complexes 1-[(η5-cyclopentadienediyl)- (η5-pentamethylcyclopentadienyl)iron(II)]-8- ferrocenylnaphthalene (5), 1-[(η5-cyclopentadienediyl) (η5-pentamethylcyclopentadienyl)rhodium(III)]-8- ferrocenylnaphthalene hexafluorophosphate (6PF6), 1-[(η5-cyclopentadienediyl)(η5- pentamethylcyclopentadienyl)iridium(III)]-8-ferrocenylnaphthalene hexafluorophosphate (7PF6), and 1-[(η6-benzene) (η5-cyclopentadienediyl)ruthenium(II)]-8-ferrocenylnaphthalene hexafluorophosphate (8PF6). The neutral complex 5 was oxidized to the paramagnetic cation 1-[(η5-cyclopentadienediyl)- (η5-pentamethylcyclopentadienyl)iron(III)]-8- ferrocenylnaphthalene hexafluorophosphate (5PF6). Compounds 3, 5PF6, 6PF6, and 7PF6 were characterized by X-ray structure determination; the neutral compound 3 crystallizes in the space group P21/c, whereas all of the cationic dinuclear complexes crystallize in the chiral space group C2221. A cyclic voltammetry study points to a predominant through-space interaction between the cationic sandwich unit and the neutral ferrocene substituent. The compounds 5PF6, 6PF6, 7PF6, and 8PF6 were subjected to hyper-Rayleigh scattering (HRS) and Kurtz-powder measurements. In both studies no SHG intensity could be observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Synthesis and reactions of ferrocenyl-capped long-chain alkynes

Alkyl-substituted acetylenes and diacetylenes with terminal ferrocenyl groups were synthesised starting from ferrocene. The reactivity of the triple bonds in the resulting compounds was used to prepare cobalt-alkyne complexes. Cyclotrimerisation of the mo

Cyclopalladated complex of 1-ferrocenylisoquinoline

A new dimeric cyclopalladated ferrocenyl complex di-μ -chloro-bis[2-(1-isoquinolinyl)ferrocenyl](C,N)dipalladium was obtained and characterized. Its catalytic properties in the Heck and Suzuki reactions (including a solid-phase version), as well as in hydroarylation of norbornene, were studied.

TRIFERROCENYL-COMPLEXE VON WOLFRAM(VI): MOLEKUELSTRUKTUR IM FESTKOERPER UND DYNAMISCHES VERHALTEN IN LOESUNG VON TRIFERROCENYL-FERROCENOXY-OXO-WOLFRAM, WO(OFc)Fc3

Triferrocenyltungsten complexes of the type WO(X)Fc3 (X=Cl, (1), OMe (2), OFc (3) and OnBu (4)) were obtained by treating WOCl4 with ferrocenyllithium, FcLi, in tetrahydrofuran solution.Reaction of WOCl4 with a threefold excess of FcLi gives 1, which may be converted into 2 using KOCH3.Reaction of WOCl4 with a sixfold excess of FcLi gives a mixture containing 3 und 4 in addition to ferrocene and biferrocene.According to the X-ray crystallographic analysis, WO(OFc)Fc3 (3) has a trigonal-bipyramidal structure with three ferrocenyl ligands occupying the equatorial positions and an axial ferrocenoxy group coordinated trans to the oxo ligand The three W-C(ferrocenyl) (average 2.092 angstroem) and the O-C(ferrocenyl) (1.33(1) angstroem) bond distances are remarkably short.The axial tungsten-oxygen distances correspond to a W=O double and a W-O single bond (1.705(5) and 1.945(5) angstroem), respectively.The 1H and 13C NMR spectra of WO(OFc)Fc3 (3) are temperature-dependent.This is ascribed to a hindered rotation of the ferrocenyl ligands around the W-C(ferrocenyl) bonds; the free activation enthalpy ΔG(excit.)(Tc) of this intramolecular dynamic process is 62.5 +/- 0.5 kJ mol-1.

Bis(ferrocenylsilyl)thiophenes and ferrocenylene(silylene) thiophene oligomers

The reaction between 1,1'-dilithioferrocene and 2,5-bis (chlorodimethylsilyl) thiophene (I), leads to a series of cyclic oligomers of basic formulation [Fc-SiMe2-TH-SiMe2](n) (II); Fc = (η5-C5H4)2Fe, TH = C4H2S. The material n = 2, IIa, has been completely characterized by spectroscopic and single crystal X-ray diffraction. Cyclic voltammetric analysis of IIa illustrates two reversible redox processes, indicating a significant interaction between the two ferrocenylene units despite the 5 atom bridge. By comparison, the monomeric analog Fc-SiMe2-TH-SiMe2-Fc (III), Fc = (η5-C5H5)Fe(η5-C5H4), prepared from the reaction of mono-lithioferrocene with I, exhibits a single redox process, even though there is the same bridge between the two Fe centers. (C) 2000 Elsevier Science Ltd.

Ferrocene-containing sterically hindered phosphonium salts

The synthesis and physical properties of the series of the ferrocenyl-containing sterically hindered phosphonium salts based on di(tert-butyl)ferrocenylphosphine is reported. Analysis of voltamogramms of the obtained compounds revealed some correlations b

Synthesis, Aromaticity and Photophysical Behaviour of Ferrocene- and Ruthenocene-Appended Semisynthetic Chlorin Derivatives

Two novel synthetic strategies to covalently link a metallocene electron-donor unit to a chlorin ring are presented. In one approach, pyropheophorbide a is readily converted into its 131-ferrocenyl dehydro derivative by nucleophilic addition of

Untersuchungen zur Darstellung und Reaktivitaet von Triferrocenylwolfram(VI)-Komplexen

A series of mononuclear triferrocenyltungsten(VI) complexes of the type WO(X)Fc3 (X=Cl, F; OMe, OEt, OnBu, OtBu, OFc) which are accessible by reaction of WOCl4 with an excess of ferrocenyllithium, FcLi, is described.A binuclear, oxo-bridged complex 2(μ-O) has also been isolated.The new compounds have been characterized on the basis of their mass spectra and their (temperature-dependent) 1H and 13C(1H) NMR spectra.

Formation of unexpected silicon- and disiloxane-bridged multiferrocenyl derivatives bearing Si-O-CHCH2 and Si-(CH2)2C(CH3)3 substituents via cleavage of tetrahydrofuran and trapping of its ring fragments

The formation of a family of silicon- and siloxane-bridged multiferrocenyl derivatives carrying different functional groups attached to silicon, including Fc2(CH3)3C(CH2)2SiCHCH2 (5), Fc2(CH2CH-O)SiCHCH2 (6), Fc2(OH)SiCHCH2 (7), Fc2(CH2CH-O)Si-O-Si(O-CHCH2)Fc2 (8) and Fc2(CH2CH-O)Si-O-SiFc3 (9) is described. Silyl vinyl ether molecules 6, 8 and 9 and the heteroleptic vinylsilane 5 resulted from the competing metathesis reaction of lithioferrocene (FcLi), CH2CH-OLi or (CH3)3C(CH2)2Li with the corresponding multifunctional chlorosilane, Cl3SiCHCH2 or Cl3Si-O-SiCl3. The last two organolithium species have been likely formed in situ by fragmentation of the tetrahydrofuran solvent. Diferrocenylvinyloxyvinylsilane 6 is noteworthy since it represents a rare example of a redox-active silyl mononomer in which two different CC polymerisable groups are directly connected to silicon. The molecular structures of the silicon-containing multiferrocenyl species 5, 6, 8 and 9 have been investigated by single-crystal X-ray diffraction studies, demonstrating the capture and storage processes of two ring fragments resulting from the cleavage of cyclic THF in redox-active and stable crystalline organometallic compounds. From electrochemical studies we found that by changing the anion of the supporting electrolyte from [PF6]- to [B(C6F5)4]-, the redox behaviour of tetrametallic disiloxane 8 can be switched from a poorly resolved multistep redox process to four consecutive well-separated one-electron oxidations, corresponding to the sequential oxidation of the four ferrocenyl moieties.

Rhodium(I) and Iridium(I) Complexes of Ferrocenyl-Functionalized Amidinates and Bis(amidinates): κ2 N-Coordination Versus Ferrocenyl Ortho-Metalation

The synthesis and characterization of two bulky ferrocenyl-functionalized amidinates and their lithium, potassium, rhodium(I), and iridium(I) complexes are reported. The ferrocenyl mono(amidine) [Fc{C(NDipp)(NHDipp)}] (1) (Fc = ferrocenyl; Dipp = 2,6-diisopropylphenyl) and its potassium complex [Fc{C(NDipp)2K}·3THF] (2) as well as the 1,1′-ferrocendiyl-bridged bis(amidinate) [fc{C(NMes)2Li}2·3THF] (3) (fc = ferrocene-1,1′-diyl; Mes = mesityl) were synthesized. Salt metathesis reactions with the metal precursors [Rh(cod)Cl]2 (cod = 1,5-cyclooctadiene) and [Ir(cod)Cl]2 gave the rhodium(I) and iridium(I) complexes [Fc{C(NDipp)2Rh(cod)}] (4), [fc{C(NMes)2Rh(cod)}2] (5), and [fc{C(NMes)2Ir(cod)}2] (6), as well as the ortho-metalated compound [(Cp)Fe(C5H3){C(NHDipp)(NDipp)Ir(cod)}] (7). As complex 7 showed an ortho-metalation on the ferrocene backbone, we investigated this reaction in more detail. It was found that the rhodium(I) complexes 4 and 5 also undergo ortho-metalation upon treatment with carbon monoxide (CO). After the carbonylation, the first known ortho-metalation of rhodium(I) on ferrocene complexes was observed for [(Cp)Fe{(C5H3)C(NHDipp)(NDipp)Rh(CO)2}] (8) and [Fe(C5H3)2{C(NHMes)(NMes)Rh(CO)2}2] (9). A combined electrochemical and quantum chemical study revealed that depending on both the metal-bound ligand (CO vs cod) and the bonding mode (κ2N vs ortho-metalated), the highest occupied molecular orbital is located more on iron or on rhodium/iridium.