7317-52-4

Usage

General Description

2,3,4,5-tetraphenylcyclopent-2-en-1-one is a chemical compound with a molecular formula C31H24O. It is a cyclic ketone with a five-membered ring structure and four phenyl groups attached to it. 2,3,4,5-tetraphenylcyclopent-2-en-1-one is a yellow crystalline solid that is used in organic synthesis and as a building block for the preparation of various advanced materials. It has been studied for its potential applications in the development of new materials for optoelectronic devices and organic light-emitting diodes. Additionally, 2,3,4,5-tetraphenylcyclopent-2-en-1-one has been investigated for its chemical and biological properties, showing potential as a sunscreen agent and as a pharmaceutical intermediate for the synthesis of bioactive compounds.

Upstream product

• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 74-85-1 ethene 
• 201230-82-2 carbon monoxide 
• 501-65-5 diphenyl acetylene 
• 100-52-7 benzaldehyde 
• 102-04-5 1,3-Diphenylpropanone 
• 100-63-0 phenylhydrazine 
• 64-19-7 acetic acid 
• 10034-85-2 hydrogen iodide 
• 854403-70-6 2-hydroxy-2,3,4,5-tetraphenyl-cyclopent-3-enone 
• 1271-28-9 nickelocene 
• 121-45-9 phosphorous acid trimethyl ester 
• 4712-55-4 diphenyl hydrogen phosphite 
• 134-81-6 benzil 

Downstream Products

• 14301-14-5 1-Oxo-2,3-diphenyl-2,3-dihydro-1H-cyclopentaphenanthren 
• 15796-67-5 1-Oxo-3-hydroxy-2,3-diphenyl-2,3-dihydro-1H-cyclopentaphenanthren 
• 60582-55-0 1,2,3,5-Tetraphenyl-4-p-(7-cycloheptatrienyl)phenyl-1,3-cyclopentadien 
• 2519-10-0 1,2,3,4,5-pentaphenylcyclopentadiene 
• 138432-23-2 C₃₀H₂₄ 
• 15570-52-2 3-methyl-1,2,4,5-tetraphenyl-cyclopenta-1,3-dien 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 

Relevant academic research and scientific papers

Protonation of Tetraphenyl- and 2,3,4-Triphenylcyclopentadienone – An NMR and X-ray Crystallographic Study

The protonation of 2,3,4,5-tetraphenylcyclopentadienone (tetracyclone) yields 6,11-diphenyl-5H-benzo[a]fluoren-5-one (17) and 2,3,4,5-tetraphenylcyclopent-2-en-1-one (18) as the major products. This contrasts with the pyrolysis of tetracyclone, which yields 5,6-diphenyl-11H-benzo[a]fluoren-11-one (22), a structural isomer of 17. Mechanisms are presented that rationalize these observations. The protonation of 4-hydroxy-2,3,4-triphenylcyclopent-2-en-1-none, the precursor to 2,3,4-triphenylcyclopentadienone, generates 2-(2′-oxo-3′,4′,5′-triphenylcyclopent-3′-enyl)-3,4,5-triphenylcyclopenta-2,4-dienone (30), which has been unequivocally characterized by X-ray crystallography. The establishment of the conformation of molecule 30 in the solid state, which correlates with the conformation in solution, provides a rationale for the subsequent formation of the tetrahydro-pentaphenyl-as-indacene-3,4-dione (32) upon further protonation.

Synthesis of multisubstituted cyclopentadienes from cyclopentenones prepared via catalytic double aldol condensation and nazarov reaction sequence

The rhenium-catalyzed synthesis of cyclopentenone derivatives via double aldol condensation and successive Nazarov reaction is described. The cyclopentenones were converted to the corresponding cyclopentadienes using organolithium reagents. Cyclopentadien

Rhodium (I)-catalyzed reductive cyclocarbonylation of internal alkynes: Atom-economic process for synthesis of 2-cyclopenten-1-ones, 5-alkylidenefuran-2(5H)-ones and indan-1-ones

The reductive cyclocarbonylation of internal alkynes with carbon monoxide catalyzed by [{RhCl(CO)2}2]/CO(NH2)2 in the presence of water has been investigated. Dialkyl alkynes underwent a reductive [2+2+1] cycloc

Hydrogenation of α,β-Unsaturated Carbonyl Compounds by Carbon monoxide and Water with Rh6(CO)16 Catalyst under Mild Conditions

By controlling such factors as the concentration of water and amine, the carbon-carbon double bond of α,β-unsaturated carbonyl compounds could be selectively hydrogenated under mild water-gas shift reaction (WGSR) conditions using a Rh6(CO)16-Et3N catalys

Rhodium carbonyl catalyzed carbonylation of unsaturated compounds. IV. Carbonylation and oligomerization of diphenylacetylene catalyzed by Co4(CO)12, Rh4(CO)12, and Ir4(CO)12 under pressure of carbon monoxide

In the presence of Co4(CO)12, Rh4(CO)12, and Ir4(CO)12 catalysts the reaction of diphenylacetylene (1) in 2-propanol under pressure of carbon monoxide gave the hydrocarbonylation products 2 and/or 3 and the oligomers 4 and/or 5, in which the ratios depended on the catalyst employed.

CYCLOPENTADIENONES IN THE REACTION OF ALKYNES WITH CYCLOPROPYLCARBENE-CHROMIUM COMPLEXES

Reaction of alkynes having bulky substituents with pentacarbonylchromium(0) (1) provided cyclopentadienone derivatives.Cyclopentadienones were easily hydrogenated to the corresponding cyclopentenones using chromium hexacarbo

Rhodium carbonyl-catalyzed carbonylation of unsaturated compounds III*. Synthesis of α,β-unsaturated ethyl ketones by cross-hydrocarbonylation of acetylenes and ethylene with carbon monoxide and hydrogen

Rhodium carbonyl-catalyzed cross-hydrocarbonylation of acetylenes and ethylene with carbon monoxide and hydrogen gives α,β-unsaturated ethyl ketones.Under CO (10 kg cm-2) and H2 (50 kg cm-2) at 90 deg C the reaction of diphenylacetylene with ethylene in the presence of Rh4(CO)12 catalyst gave (E)-1,2-diphenyl-1-penten-3-one (3a) in 91percent yield.Under similar conditions phenylacetylene (1d), 1-hexyne (1e), 3,3-dimethyl-1-butyne (1f), and trimethylsilylacetylene (1g) gave (E)-1-phenyl-1-penten-3-one (3d), (E)-4-nonen-3-one (3e), (E)-6,6-dimethyl-4-hepten-3-one (3f), and (E)-1-trimethylsilyl-1-penten-3-one (3g) in 76, 68, 93, and 62percent respectively.Thus, the reaction of terminal acetylenes proceeds with high stereo- and regioselectivity: the propionyl group is introduced to the less-sterically hindered acetylenic carbon atom.By comparison of the regioselectivity with that in the formation of 5-ethyl-2-(5H)-furanone (2), which is obtained in the presence of a hydrogen donor such as alcohol, these reactions are assumed to include a β-acylvinylrhodium complex as the common key intermediate.

ORGANIC CHEMISTRY OF SUBVALENT TRANSITION METAL COMPLEXES XI. OXIDATIVE ADDITIONS OF NICKEL(0) COMPLEXES TO CARBON-CARBON BONDS IN ALKYNES: NICKELIRENES AND NICKELOLES AS CATALYTIC CARRIERS IN THE OLIGOMERIZATION OF ALKYNES

The formation of 2,3,4,5-tetraphenylnickelole-bis(triphenylphosphine) (IIIa) and 2,3,4,5-tetraphenylnickelole-bis(1,2-diphenylphosphino)ethane (IIIb), either from (E,E)-1,2,3,4-tetraphenyl-1,3-butadien-1,4-ylidenedilithium (I) and the corresponding nickel(II) chloride-phosphine complexes (II) or from the reduction of η4-tetraphenylcyclobutadienenickel(II) bromide dimer (XII) in the presence of phosphines, proceeds in good yields.Nickelole IIIa displays physical and chemical properties consistent with its structure and is a catalyst for the trimerization of diphenylacetylene.Nickelole IIIb is a highly associated structure but in its chemical response to alkynes, HOAc, O2, Br2, NaAlEt2H2 and heat displays the properties of a nickelole, rather than a cyclobutadienenickel(0) complex.Attempts to generate IIIb photochemically from η4-1,5-cyclooctadiene(η4-tetraphenylcyclopentadienone)nickel and diphos failed, but it was shown that structural types, such as η4-tetraphenylcyclopentadienone(diphos)nickel (a model for the structure suggested by Hoberg and Richter for IIIb), are unstable.Oligomerizations of diphenylacetylene by bis(1,5-cyclooctadiene)nickel were retarded by conducting the reaction in THF or in the presence of diphos.This retardation permitted the interception of products (cis-stilbene and (E,E)-1,2,3,4-tetraphenyl-1,3-butadiene)diagnostic for the intermediacy of nickelirenes and nickeloles.Deuterium labeling verified the presence of carbo-nickel bonds.These trapping experiments, together with findings on the thermal behavior of nickeloles, are combined into a comprehensive view of the cyclotrimerization, cyclotetramerization and linear polymerization of alkynes by nickel(0).