33504-08-4

Basic information

• Product Name: triscarbonyl-(η⁴-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)iron
• Synonyms: triscarbonyl-(η⁴-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)iron
• CAS NO: 33504-08-4
• Molecular Weight: 524.355
• Mol File: 33504-08-4.mol

Chemical Properties

• CAS DataBase Reference: triscarbonyl-(η⁴-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)iron(CAS DataBase Reference)
• NIST Chemistry Reference: triscarbonyl-(η⁴-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)iron(33504-08-4)
• EPA Substance Registry System: triscarbonyl-(η⁴-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)iron(33504-08-4)

Safety Data

• Hazardous Substances Data: 33504-08-4(Hazardous Substances Data)

Upstream product

• 668-29-1 3,4-bis(4-methoxyphenyl)-2,5-diphenyl-2,4-cyclopentadien-1-one 
• 13463-40-6 iron pentacarbonyl 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 15321-51-4 diiron nonacarbonyl 
• 17685-52-8 triiron dodecarbonyl 
• 2858-02-8 4,5,6,7-tetraphenyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-8-one 

Downstream Products

• 75812-19-0 dicarbonyl(η4-tetraphenylcyclopentadienone)(trimethyl phosphite)iron 
• 17685-52-8 triiron dodecarbonyl 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 

Relevant articles and documents

Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations

Four (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds were synthesized, and their activities in transfer hydrogenations of carbonyl compounds and transfer dehydrogenations of alcohols were explored and compared to those of the well-established [2,5-(SiMe3)2-3,4-(CH2)4(η4-C4C=O)]Fe(CO)3 (3). A new compound, [2,5-bis(3,5-dimethylphenyl)-3,4-diphenylcyclopentadienone]iron tricarbonyl (7), was the most active catalyst in both transfer hydrogenations and dehydrogenations, and compound 3 was the least active catalyst in transfer hydrogenations. Evidence was found for product inhibition of both 3 and 7 in a transfer dehydrogenation reaction, with the activity of 3 being more heavily affected. A monomeric iron hydride derived from 7 was spectroscopically observed during a transfer hydrogenation, and no diiron bridging hydrides were found under reductive or oxidative conditions. Initial results in the transfer hydrogenation of N-benzylideneaniline showed that 3 was a significantly less active catalyst in comparison to the (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds.

Synthesis of functionalized iron N-heterocyclic carbene complexes and their potential application as flame behavior modifier in cross linked epoxy resins

The design of new flame retardants (FR) that avoid the use of halogen and phosphorus additives is challenging and urgent. Herein we report on the synthesis of bis-amino functionalized N-heterocyclic carbene cyclopentadienone iron complexes aimed at promot

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts

The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

Iron-catalyzed selective production of methyl esters from aldehydes

A process for making methyl esters in high yields is provided. The process comprises contacting aliphatic or aromatic aldehydes and methanol with an iron catalyst, to catalyze the dehydrogenative coupling between aliphatic or aromatic aldehydes and methanol. The reaction is highly selective (99.9%) toward the formation of methyl esters over homoesters and alcohols and operates at temperatures of less than 100° C. for 2-8 hours.

Discovery of a Photoinduced Dark Catalytic Cycle Using in Situ LED-NMR Spectroscopy

We report the use of LED-NMR spectroscopy to study the reaction mechanism of a newly discovered photoinduced iron-catalyzed cycloisomerization of alkynols to cyclic enol ethers. By understanding on/off ligand binding to the catalyst, we were able to appro

New air-stable iron catalyst for efficient dynamic kinetic resolution of secondary benzylic and aliphatic alcohols

We herein report a catalyst system for the dynamic kinetic resolution of secondary alcohols by combining the enzymatic resolution with an iron-catalyzed racemization. A new air-stable tricarbonyl (cyclopentadienone)iron complex is identified as the active racemization catalyst for this transformation without any additive. Various substrates including benzylic, heteroaromatic, aliphatic alcohols can be used and afford the corresponding esters in good yields and with excellent enantioselectivities.

Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination

Reductive amination under hydrogen pressure is a valuable process in organic chemistry to access amine derivatives from aldehydes or ketones. Knoelker's complex has been shown to be an efficient iron catalyst in this reaction. To determine the influence of the substituents on the cyclopentadienone ancillary ligand, a series of modified Knoelker's complexes was synthesised and fully characterised. These complexes were also transformed into their analogous acetonitrile iron-dicarbonyl complexes. Catalytic activities of these complexes were evaluated and compared in a model reaction. The scope of this reaction is also reported. For mechanistic insights, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Festival of amination: Two series of modified Knoelker's complexes were synthesised and applied in the reductive amination of various carbonyl derivatives with primary or secondary amines (see scheme, TIPS = triisopropylsilyl). For a mechanistic insight, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Copyright

(Cyclopentadienone)iron shvo complexes: Synthesis and applications to hydrogen transfer reactions

A series of (cyclopendienone)iron tricarbonyl complexes were prepared using an intramolecular cyclization strategy. These were applied to the catalysis of the oxidation of alcohols to aldehydes and ketones. When paraformaldehyde was used as the hydrogen acceptor, formate esters were obtained as coproducts and, in several cases, the major products.

Electrochemistry of iron and ruthenium flyover bridge complexes

The redox chemistry of dimetallacycloheptadiene (flyover bridge) complexes M2(CO)6[C(R)=C(R′)COC(R″)=(R?)] (M = Fe or Ru) has been investigated by electrochemical and spectroscopic techniques. For the Fe2(CO)6[(PhC2Ph)2CO] derivative the bulk of the data indicates a sequence of electrochemical events involving the formation of the monoanion and its decomposition to solvated [Fe(CO)3]- and Fe(CO)3[(PhC2Ph)2CO] fragments, which are able to recombine together on electrochemical or chemical reoxidation giving back the parent complex. Electron paramagnetic resonance features of electroreduced solutions of 13CO-enriched sample of Fe2(CO)6[(PhC2Ph)2CO] and its monophosphine derivative Fe2(CO)5(PPh)3[(PhC2Ph) 2CO] lend support to the proposed mechanism. The influence of the dienone substituents, R, as well as the effect of the replacement of group V (15) donor ligands for CO on the trend of the electrode potentials is discussed.

Pentacarbonyliron-promoted Conversion of 3a,7a-Dihydroindenones into Indanones

Reactions of 3a-7a-dihydroindenones or 3a,4,7,7a-tetrahydro-4,7-methanoindene-1,8-diones with Fe(CO)5 afford indanones as the sole products.No corresponding diene-Fe(CO)3 complexes have been detected.The mechanisms for these reactions are established on the basis of deuterium-labelling experiments.