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Cas Database

119-61-9

119-61-9

Identification

  • Product Name:Benzophenone

  • CAS Number: 119-61-9

  • EINECS:204-337-6

  • Molecular Weight:182.222

  • Molecular Formula: C13H10O

  • HS Code:29143900

  • Mol File:119-61-9.mol

Synonyms:Methanone, diphenyl-;alpha-Oxoditane;Kayacure BP;Benzene, benzoyl-;Diphenyl ketone;Ketone, diphenyl;Diphenylketone;alpha-oxodiphenylmethane;Diphenylmethanone;Phenyl ketone;Benzophenone Flakes;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,DangerousN,FlammableF HarmfulXn

  • Hazard Codes:Xi,N,Xn,F

  • Signal Word:Warning

  • Hazard Statement:H373 May cause damage to organs through prolonged or repeated exposureH412 Harmful to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse and then wash skin with water and soap. In case of eye contact Rinse with plenty of water (remove contact lenses if easily possible). If swallowed Rinse mouth. Ingestion causes gastrointestinal disturbances. Contact causes eye irritation and, if prolonged, irritation of skin. (USCG, 1999) /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ketones and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Flash point data for this chemical are not available, but it is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants. Store in an area without drain or sewer access.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature -20°C.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 2306 Articles be found

Substituent and Solvent Effects in the Reactions of Diaryldiazomethanes with 2,3-Dichloro-5,6-dicyanobenzoquinone

Oshima, Takumi,Nagai, Toshikazu

, p. 2039 - 2044 (1981)

Kinetic studies have been made of the reactions of fifteen meta- and para-substituted diphenyldiazomethanes(DDMs) with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in benzene.The second order rate constants, k, increased with the electron-donability of the substituents, and the value could be correlated with the Yukawa-Tsuno equation: log k/k0 = -2.33(?0 + 0.47Δ+) + 0.017, (r = 0.996, 30 deg C).The ρ value, -2.33, indicates the development of a positive charge at the diazo carbon in the transition state, while the R value, 0.47, confirms the moderate stabilization of the positive charge by the ?-electronic contribution of the para substituents.The rate constants have also been determined for the reaction of diphenyldiazomethane(DDM) with DDQ in 28 aprotic solvents.The effects of solvents can be interpreted in terms of the basicity and the steric nature of the solvents.The products of these reactions were poly(2,3-dichloro-5,6-dicyanohydroquinone benzhydryl ether)s, which were easily convertible into benzophenones and α,α-dimethoxydiphenylmethane, together with 2,3-dichloro,5,6-dicyanohydroquinone, under the influence of water and methanol.These solvolysis products were also obtained in excellent yields in the initial presence of these additives.

COMPARISON OF PHOTOINDUCED ELECTRON TRANSFER REACTIONS OF AROMATIC CARBONYL VS. CYANO COMPOUNDS WITH ELECTRON DONORS IN CONDENSED PHASE: THE IMPORTANCE OF THE SPIN STATE OF THE GEMINATE ION PAIR FOR OBTAINING HIGH ION YIELDS.

Haselbach, Edwin,Vauthey, Eric,Suppan, Paul

, p. 7335 - 7344 (1988)

Photoinduced electron transfer reactions in acetonitrile with benzophenone, anthraquinone, 9-cyanoanthracene and 9,10-dicyanoanthracene as electron acceptors, and with 1,4-diazabicyclooctane and N,N-dimethylaniline as electron donors have been studied with ns-laser flash photolysis and fluorescence quenching measurements.For these systems the resulting free ion yield depends on the spin state of the geminate ion pair: its separation is very efficient if formed in a triplet state (carbonyl compounds/donors), while it is very inefficient if formed in a singlet state (cyanoantracenes/donors).In the triplet systems, geminate back electron transfer is limited by the rate of spin flip.

Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of alcohols

Sakuramoto, Takashi,Donaka, Yosuke,Tobisu, Mamoru,Moriuchi, Toshiyuki

, p. 17571 - 17576 (2019)

Oxovanadium(v)-catalyzed transformation of alcohols in the presence of hydrazine derivatives was demonstrated. The direct hydrazination reaction of 1,3-diphenylprop-2-en-1-ol with 1,1-diphenylhydrazine in the presence of VO(OSiPh3)3 as a catalyst and MS3A as a dehydrating reagent proceeded to afford the corresponding hydrazination product. On the contrary, the utilization of 1,1-dimethylhydrazine instead of 1,1-diphenylhydrazine was found to induce the deoxygenative homocoupling reaction of the allyl alcohol to give the corresponding 1,5-diene as a major product. In addition to the deoxygenative homocoupling product, the allyl amine into which aniline was introduced was also obtained by using 1,2-diphenylhydrazine in the reaction of 1,3-diphenyl-2-methylprop-2-en-1-ol. Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of benzyl alcohols could also be performed in the presence of 1,1-dimethylhydrazine.

Ligand-free palladium-catalyzed aerobic oxidative coupling of carboxylic anhydrides with arylboronic acids

Yin, Weiyan,He, Haifeng,Zhang, Yani,Long, Tong

, p. 2402 - 2406 (2014)

We report a new, effective and environmentally friendly protocol for selective aerobic oxidative coupling of arylboronic acids with carboxylic anhydrides in the presence of ligand-free palladium catalyst. The aryl benzoates are obtained in good to excellent yields.

-

Kharasch,Nudenberg,Archer

, p. 495,497 (1943)

-

-

Zeiss

, (1951)

-

Co(ii)-cluster-based metal-organic frameworks as efficient heterogeneous catalysts for selective oxidation of arylalkanes

Fan, Yanru,Li, Xiao,Gao, Kuan,Liu, Yu,Meng, Xiangru,Wu, Jie,Hou, Hongwei

, p. 1666 - 1673 (2019)

To explore metal-organic frameworks (MOFs) based on Co-clusters as heterogeneous catalysts to selectively catalyze the reaction of C-H bond oxidation of aromatic alkanes to their corresponding ketones, three MOFs {[Co5(pmbcd)2(μ3-OH)2(H2O)4(DMF)2]·4DMF}n (MOF 1), {[Co2(pmbcd)(bpea)2]·2H2O·2DMF}n (MOF 2), and {[Co2(pmbcd)(dpp)2]·3H2O·2DMF}n (MOF 3) (H4pmbcd = 9,9′-(1,4-phenylenebis(methylene))bis(9H-carbazole-3,6-dicarboxylic acid), bpea = 1,2-bis(4-pyridyl)ethane, dpp = 1,3-di(4-pyridyl)propane) were successfully synthesized and structurally characterized. MOF 1 was constructed from a pentanuclear Co(ii) cluster and exhibited a porous framework with channels of 8 × 10 ?2 along the b axis. MOF 2 was constructed from [Co2(CO2)4] units and presented a porous three-dimensional (3D) framework with channels of 11 × 13 ?2 along the b axis and of 10 × 12 ?2 along the c axis. MOF 3 was a flat two-dimensional (2D) layer based on binuclear Co(ii) units when dpp as an auxiliary ligand was introduced. The Co5-cluster-based MOF 1 exhibited excellent catalytic activity for the direct C-H bond activation of arylalkanes to ketones in H2O under room temperature because of its high density of Lewis acidic sites within the frameworks and suitable channel size to access the catalytic sites. It also presented the spatial confinement effect and catalyzed the reaction with high regioselectivity, forming mono-ketones as the sole products. Easy product separation, simple reaction procedures, and recyclability of these catalysts make the catalytic system attractive. Our work highlights the superiority of the MOF-based materials as heterogeneous catalysts.

Oxidation of phenylhydrazones of α-keto esters with hypervalent organoiodine reagents

Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Shinada, Tetsuro

, p. 7191 - 7194 (1993)

α-Ketoacids and ketones can easily be regenerated in high yield from their phenylhydrazones via hydroxy azo compounds upon oxidation with hupervalent iodine reagents.

Ionic liquid [bmim]Br assisted chemoselective benzylic [Formula presented] oxidations using tert-butyl hydroperoxide

Naidu, Shivaji,Reddy, Sabbasani Rajasekhara

, p. 441 - 445 (2016)

A mild and efficient, ionic-liquid-assisted green protocol for the chemoselective oxygenation of benzylic C-H bonds to corresponding ketones using ionic liquid [bmim]Br with tert-butyl hydroperoxide has been developed. The method reported in this paper has the advantages of [bmim]Br acting as recyclable solvent and reagent. The usage of additives such as acids or bases and metal salts is not required. The developed strategy is further extended to oxidation of secondary alcohols to respective ketones under similar optimized reaction conditions.

Mechanism of thermal decomposition of diphenyldiazomethane in the presence of oxygen

Komissarov,Nazarov,Yamilova

, p. 261 - 264 (1997)

The kinetics, products, and mechanism of thermal decomposition of diphenyldiazomethane (RN2, R = Ph2C) in the presence of oxygen were studied. Thermolysis is accompanied by chemiluminescence. An-emitter of chemiluminescence (3RO) forms in the reaction of benzophenone 0-oxide ROO with RN2.

Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate

Savarin, Cecile,Srogl, Jiri,Liebeskind, Lanny S.

, p. 3229 - 3231 (2000)

(matrix presented) Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-n-butyl thiol esters were most effective in this cross-coupling.

Kinetics, products, and mechanism of the reaction of diphenylcarbonyl oxide with sulfoxides

Nazarov,Chainikova,Krupin,Khursan,Kalinichenko,Komissarov

, p. 1496 - 1500 (2000)

The kinetics of the reactions of diphenylcarbonyl oxide with dimethyl, di-n-hexyl, diphenyl, dibenzyl, and n-hexylbenzyl sulfoxides in acetonitrile was studied by flash photolysis at 295 K. The oxidation of sulfoxide affords the corresponding sulfone as t

Product selectivity in semiconductor-mediated dehydrazonation of benzophenone hydrazone

Krishnakumar,Selvam,Swaminathan

, p. 1929 - 1937 (2011)

Product selectivity in the dehydrazonation of benzophenone hydrazone by photocatalytic oxidation with various semiconductor photocatalysts has been investigated using ultraviolet-A light. TiO2-P25 shows greater product selectivity of benzophenone formation with 93.9% conversion. Doping of metals on TiO2 selectively enhances the formation of azine from hydrazone. Solvents such as dichloromethane, chloroform, and dichloroethane also enhance the formation of azine.

Solid phase synthesis of α-acylamino-α,α-disubstituted ketones

Tice, Colin M.,Michelotti, Enrique L.,Mata, Ernesto G.,Nicolàs, Ernesto,Garcia, Javier,Albericio, Fernando

, p. 7491 - 7494 (2002)

α-Acylamino-α,α-disubstituted ketones are of interest as ecdysone agonists. Solid phase synthesis of prototypical α-acylamino-α,α-disubstituted ketones on two different solid supports is described. In both cases the ketone was formed by reaction of a Grignard reagent with an N-acyl-α,α-disubstituted amino acid immobilized through its carboxylate as a Weinreb amide derivative.

Heteropolytungstic acids incorporated in an ordered mesoporous zirconia framework as efficient oxidation catalysts

Skliri, Euaggelia,Lykakis, Ioannis N.,Armatas, Gerasimos S.

, p. 8402 - 8409 (2014)

Ordered mesoporous composite catalysts consisting of nanocrystalline tetragonal ZrO2 and heteropolytungstic clusters, i.e. 12-phosphotungstic (PTA) and 12-silicotungstic (STA) acids, were prepared via a surfactant-assisted co-polymerization route. According to the X-ray diffraction, transmission electron microscopy and N2 physisorption measurements, the resultant materials possess a well-defined mesoscopic order ranging from wormhole to hexagonal pore structure and exhibit large internal surface area (126-229 m2 g-1) and quite narrow pore size distribution (ca. 2.2-2.6 nm in diameter). Energy dispersive X-ray microanalysis and infrared spectroscopy confirms that the heteropoly clusters are well dispersed within the zirconia matrix, while preserving intact their Keggin structure. The inclusion of PTA and STA clusters in the mesoporous framework has a beneficial effect on the catalytic activity of these materials. Although zirconium oxide and heteropoly acids alone show little catalytic activity, the ZrO 2-PTA and ZrO2-STA heterostructures exhibit surprisingly high activity in hydrogen peroxide mediated oxidation of 1,1-diphenyl-2- methylpropene under mild conditions. Indeed, the mesoporous ZrO2-STA composite sample loaded with 5 wt% STA shows a conversion rate that is 17 times higher than the mesoporous ZrO2. The catalytic activity of these materials is related to the spatial distribution of heteropoly acids in zirconia matrix and possible synergistic interactions between the incorporated Keggin units and Zr(iv) oxohydroxide species.

A simple synthesis of symmetrical α-diones from organometallic reagents and 1,4-dimethyl-piperazine-2,3-dione

Mueller-Westerhoff, Ulrich T.,Zhou, Ming

, p. 571 - 574 (1992)

Short reflux of an equimolar mixture of N-N′-dimethyl ethylenediamine and diethyl oxalate in ipropanol or diethyl ether leads to 1,4-dimethyl-piperazine-2,3-dione, which is able to react with two equivalent of organolithium or Grignard compounds to form symmetrically substituted α-diones in excellent yields.

Use of Isopropyl Alcohol as a Reductant for Catalytic Dehydoxylative Dimerization of Benzylic Alcohols Utilizing Ti?O Bond Photohomolysis

Iwasawa, Nobuharu,Sumiyama, Keiichi,Toriumi, Naoyuki

, p. 2474 - 2478 (2021)

Photohomolysis of Ti?O bonds is utilized in photocatalytic generation of titanium(III) species for dehydroxylative dimerization of benzylic alcohols under UV-light irradiation by using isopropyl alcohol (IPA) as a stoichiometric reductant. In this reaction, IPA works not as a single-electron donor as in the photo-redox catalyzed reactions but as an H-atom-donor. The reaction also proceeds under visible-light irradiation in the presence of thioglycolic acid as a ligand.

TWO INTERMEDIATES OBSERVED IN THE GRIGNARD REACTION WITH BENZOPHENONE

Maruyama, Kazuhiro,Hayami, Jun-ichi,Katagiri, Toshimasa

, p. 601 - 604 (1986)

Intermediates in the reaction of Grignard reagent with benzophenone in THF were investigated by both ESR and stopped-flow techniques.The short-lived (blue colored) and other long-lived (pink colored radical) intermediates were observed.The pink colored radical intermediate could be in a state of dimeric aggregate of benzophenone anion radicals ion-paired with Grignard cation + in solution.

Sisti,Milstein

, p. 2408 (1973)

Phosphine-free NiBr2-catalyzed synthesis of unsymmetrical diaryl ketones via carbonylative cross-coupling of aryl iodides with Ph3SnX (X = Cl, OEt)

Iranpoor, Nasser,Firouzabadi, Habib,Etemadi-Davan, Elham

, p. 282 - 287 (2015)

Abstract The convenient nickel-catalyzed carbonylative coupling of aryl iodides with Ph3SnCl or Ph3SnOEt for synthesis of unsymmetrical diaryl ketones under phosphine-free condition is reported. The reaction occurs efficiently in the presence of Cr(CO)6 as an easy handling solid source of carbon monoxide at atmospheric pressure and 100 °C in DMF under air to deliver the desired ketones in high yield.

Oxidation of Benzylic Methylene Compounds to Ketones with 4-Aminoperoxybenzoic Acid Supported on Silica Gel in Presence of Oxygen or Air

Hashemi, Mohammed M.,Ghazanfari, Dadkhoda,Karimi-Jaberi, Zahed

, p. 185 - 188 (2004)

4-Aminoperoxybenzoic acid supported on silica gel in presence of oxygen or air was found to be a convenient and selective oxidant for the oxidation of benzylic methylene compounds to the corresponding ketones.

Benzimidazole-based palladium-N-heterocyclic carbene: A useful catalyst for C-C cross-coupling reaction at ambient condition

Gupta, Sumanta,Basu, Basudeb,Das, Sajal

, p. 122 - 128 (2013)

A convenient way for the synthesis of benzimidazole-based Pd-N-heterocyclic carbene complex and its structural characterization are described. The complex efficiently catalyzes Suzuki cross-coupling reaction in a wide variety of substrates including heteroaromatic system at ambient condition. The catalyst is also effective for multi Suzuki cross-coupling reaction. In addition, the catalyst is equally active toward C-C cross-coupling reaction between acid chloride and arylboronic acid, giving the desired ketones in high yield.

A Tale of Copper Coordination Frameworks: Controlled Single-Crystal-to-Single-Crystal Transformations and Their Catalytic C-H Bond Activation Properties

Chen, Yifa,Feng, Xiao,Huang, Xianqiang,Lin, Zhengguo,Pei, Xiaokun,Li, Siqing,Li, Jikun,Wang, Shan,Li, Rui,Wang, Bo

, p. 13894 - 13899 (2015)

Metal-organic frameworks (MOFs), as a class of microporous materials with well-defined channels and rich functionalities, hold great promise for various applications. Yet the formation and crystallization processes of various MOFs with distinct topology, connectivity, and properties remain largely unclear, and the control of such processes is rather challenging. Starting from a 0D Cu coordination polyhedron, MOP-1, we successfully unfolded it to give a new 1D-MOF by a single-crystal-to-single-crystal (SCSC) transformation process at room temperature as confirmed by SXRD. We also monitored the continuous transformation states by FTIR and PXRD. Cu MOFs with 2D and 3D networks were also obtained from this 1D-MOF by SCSC transformations. Furthermore, Cu MOFs with 0D, 1D, and 3D networks, MOP-1, 1D-MOF, and HKUST-1, show unique performances in the kinetics of the C-H bond catalytic oxidation reaction.

Electron Transfer Catalyzed Reactions. Electrochemical Induction of the Hydrogen Atom Transfer Oxidation of Alcohols and Other Substrates by Aromatic Halides

Andrieux, Claude P.,Badoz-Lambling, Jeanine,Combellas, Catherine,Lacombe, Daniel,Saveant, Jean-Michel,et al.

, p. 1518 - 1525 (1987)

The reduction of aryl halides in the presence of primary or secondary alcohols in liquid ammonia or in pure alcohol leads to the formation of the corresponding carbonyl compounds along an elctrocatalytic process consuming a vanishingly small amount of electricity.The aryl radical generated upon electrochemical reductive cleavage of the aryl halide first abstracts a H atom from the alcohol leading to an hydroxyalkyl radical which deprotonates into the ketyl anion radical, which is itself oxidized into the carbonyl compound.Side reactions are the reduction of the aryl radical and of the hydroxyalkyl radical.A detailed study of the feasibility and the mechanism of the reacton has been carried out by cyclic voltammetry and preparative scale electrolysis.The results underscore the fact that besides its acid-base properties, the H-atom donation ability of the solvent can play an important role in the course of electrochemical reactions.The electron stoichiometry, varying between 0 and 2, and the product distribution are functions of the redox and acid-base properties of the radical resulting from H-atom abstraction and of the redox and cleavage characteristic of the aryl halide anion radical.The reaction allows the oxidation of a large variety of substrates under electrochemically reducing conditions, those which lead to the formation of the aryl radical from the starting aryl halide.

Fabrication of CuCr2O4 spinel nanoparticles: A potential catalyst for the selective oxidation of cycloalkanes via activation of Csp3-H bond

Acharyya, Shankha S.,Ghosh, Shilpi,Adak, Shubhadeep,Tripathi, Deependra,Bal, Rajaram

, p. 145 - 150 (2015)

We report here preparation of CuCr2O4 spinel nanoparticle catalyst, mediated by cationic surfactant CTAB in hydrothermal route. XRD revealed the formation of CuCr2O4 spinel phase and TEM showed the particle size of 30-60 nm. The catalyst was speculated to be highly active for selective oxidation of cyclohexane to cyclohexanone with H2O2. A cyclohexane conversion of 70% with 85% cyclohexanone selectivity was achieved over this catalyst at 50 °C temperature. Moreover, the catalyst did not show any significant activity loss even after 8 reuses and proved its efficacy in the oxidation of other cycloalkanes also.

-

Lapkin,Ljubimowa

, (1950)

-

Ayres,Hauser

, p. 116,118 (1948)

Fe3O4@dopa (dopa = dopamine hydrochloride) functionalized Mn(III) Schiff base complex: A promising magnetically separable heterogeneous catalyst for oxidative transformations

Chakraborty, Aratrika,Chattopadhyay, Tanmay

, p. 3293 - 3307 (2017)

A chiral Schiff base complex has been prepared by treating (R)-1,2-diaminopropane with 3,5-dichlorosalicylaldehyde in ethanol, followed by addition of manganese chloride hexahydrate to generate a homogeneous catalyst, [MnL(Cl)(H2O)] (HMN). Crystal structure of the complex reveals its mononuclear nature. Circular dichroism (CD) studies indicate that the ligand and its corresponding complex contain an asymmetric center. The catalytic activity of HMN toward epoxidation of alkenes, oxidation of alcohols and oxidation of alkanes has been investigated in the presence of iodosylbenzenediacetate (PhI(OAc)2), in acetonitrile. In the present work we found yields to be much higher compared to our previous approaches. For further adaptation, we attached our efficient homogeneous catalyst with surface modified magnetic nanoparticles (Fe3O4@dopa) and thereby obtained a new magnetically separable nanocatalyst Fe3O4@dopa@MnLCl (FDM). This catalyst has been characterized and its oxidation ability assessed in similar conditions as those used for the homogeneous catalyst. Enantiomeric excess in epoxide yield reveals retention of chirality of the active site of Fe3O4@dopa@MnLCl. The catalyst can be recovered by magnetic separation and recycled several times without significant loss of catalytic activity.

Bioinspired oxidation of oximes to nitric oxide with dioxygen by a nonheme iron(II) complex

Bhattacharya, Shrabanti,Lakshman, Triloke Ranjan,Sutradhar, Subhankar,Tiwari, Chandan Kumar,Paine, Tapan Kanti

, p. 3 - 11 (2020)

The ability of two iron(II) complexes, [(TpPh2)FeII(benzilate)] (1) and [(TpPh2)(FeII)2(NPP)3] (2) (TpPh2 = hydrotris(3,5-diphenylpyrazol-1-yl)borate, NPP-H = α-isonitrosopropiophenone), of a monoanionic facial N3 ligand in the O2-dependent oxidation of oximes is reported. The mononuclear complex 1 reacts with dioxygen to decarboxylate the iron-coordinated benzilate. The oximate-bridged dinuclear complex (2), which contains a high-spin (TpPh2)FeII unit and a low-spin iron(II)–oximate unit, activates dioxygen at the high-spin iron(II) center. Both the complexes exhibit the oxidative transformation of oximes to the corresponding carbonyl compounds with the incorporation of one oxygen atom from dioxygen. In the oxidation process, the oxime units are converted to nitric oxide (NO) or nitroxyl (HNO). The iron(II)–benzilate complex (1) reacts with oximes to afford HNO, whereas the iron(II)–oximate complex (2) generates NO. The results described here suggest that the oxidative transformation of oximes to NO/HNO follows different pathways depending upon the nature of co-ligand/reductant.

Sonovoltammetric measurement of the rates of electrode processes with fast coupled homogeneous kinetics: Making macroelectrodes behave like microelectrodes

Compton, Richard G.,Marken, Frank,Rebbitt, Thomas O.

, p. 1017 - 1018 (1996)

Voltammetric measurements of the rates of fast homogeneous chemical reactions coupled to heterogeneous electron transfer at macroelectrodes are demonstrated for two systems, the reductive dehalogenations of ortho-bromonitrobenzene and of 3-bromobenzophenone, by the use of power ultrasound to confer fast mass-transport properties so giving the electrodes the kinetic timescale of microelectrodes.

-

Gilman,St. John

, p. 1172,1176 (1930)

-

Azolium/Hydroquinone Organo-Radical Co-Catalysis: Aerobic C?C-Bond Cleavage in Ketones

Nakatsuji, Yuya,Kobayashi, Yusuke,Masuda, Sakyo,Takemoto, Yoshiji

, p. 2633 - 2637 (2021)

Organo-radical catalysts have recently attracted great interest, and the development of this field can be expected to broaden the applications of organocatalysis. Herein, the first example of a radical-generating system is reported that does not require any photoirradiation, radical initiators, or preactivated substrates. The oxidative C?C-bond cleavage of 2-substituted cyclohexanones was achieved using an azolium salt and a hydroquinone as co-catalysts. A catalytic mechanism was proposed based on the results of diffusion-ordered spectroscopy and cyclic voltammetry measurements, as well as computational studies.

Kinetic studies of lipid phase autoxidation of diphenylmethane

Okada,Kitamura,Hayakawa

, p. 281 - 289 (1971)

-

RADICAL CATION INTERMEDIATES IN THE FORMATION OF SCHIFF BASES ON IRRADIATED SEMICONDUCTOR POWDERS

Fox, Marye Anne,Younathan, Janet N.

, p. 6285 - 6292 (1986)

Photocatalytic oxidation of several primary aliphatic amines on irradiated TiO2 powders suspended in anhydrous acetonitrile led to good yields of the corresponding symmetrical N-alkylidene amines.Mechanistic electrochemical investigation of the reaction revealed intermediate formation of an immonium cation in an ECE route.This species is generated via electrooxidation of an α-amino radical formed by deprotonation of the primary oxidation product, an aminium cation radical.The influence of the metal oxide surface on radical cation reactivity is discussed.

Rh-catalyzed carbonylation of arylzinc compounds yielding symmetrical diaryl ketones by the assistance of oxidizing agents

Kobayashi, Kana,Nishimura, Yugo,Gao, Fuxing,Gotoh, Kazuma,Nishihara, Yasushi,Takagi, Kentaro

, p. 1949 - 1952 (2011)

Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh-dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts induced oxidative homocoupling of 1 to yield biaryls instead. The beneficial catalysis by Rh in the carbonylation was presumed to stem from the facility by which the migration of the aryl ligand to CO at the Rh3+ intermediate occurred.

A new synthesis of selenol esters via carbophilic addition of organocopper reagents to carbonyl selenide

Fujiwara, Shin-Ichi,Asai, Akira,Shin-Ike, Tsutomu,Kambe, Nobuaki,Sonoda, Noboru

, p. 1724 - 1726 (1998)

-

Liquid phase oxidation of diphenylmethane to benzophenone with molecular oxygen over nano-sized Co-Mn catalyst supported on calcined Cow bone

Monjezi,Yazdani,Mokfi,Ghiaci

, p. 58 - 63 (2014)

A well-dispersed Co-Mn catalyst immobilized on calcined Cow bone was synthesized and used, for the first time for the selective synthesis of benzophenone by liquid phase oxidation of diphenylmethane under various reaction conditions. The catalyst was characterized using techniques such as UV-vis, SEM, TEM and BET. The catalyst has shown an excellent activity (87%), selectivity to diphenyl ketone (90%) and stability under solvent free conditions. To investigate the leaching of the metals from the support, results of the original and reusable catalyst was correlated and compared, and the catalytic activity of washed catalyst was also demonstrated. Based on the all catalytic results for this reaction, the new catalyst was found to be a highly active and environmentally friendly solid catalyst and has superior catalytic activity.

Dittmer,Whitman

, p. 2004 (1969)

Chloro-ruthenium complexes with carbonyl and N-(aryl)pyridine-2-aldimines as ancillary ligands. Synthesis, characterization and catalytic application in C-C cross-coupling of arylaldehydes with arylboronic acids

Dey, Bikash Kali,Dutta, Jayita,Drew, Michael G.B.,Bhattacharya, Samaresh

, p. 176 - 184 (2014)

Reaction of N-(aryl)pyridine-2-aldimines (L-R, R = OCH3, CH 3, H, Cl and NO2) with [Ru(CO)2Cl 2]n in refluxing ethanol affords a group of complexes of type [Ru(L-R)(CO)2Cl2]. In these complexes the diimine ligands (L-R) are coordinated to the metal center as NN-donors forming five-membered chelate rings, the carbonyls are mutually cis and the two chlorides are trans. Crystal structure of [Ru(L-OCH3)(CO) 2Cl2] has been determined. All the complexes show characteristic 1H NMR signals, and in dichloromethane solution they display intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows an irreversible oxidation of the metal center within 1.15-1.23 V vs SCE, and reduction(s) of the diimine ligand within -0.70 to -0.96 V vs SCE. The [Ru(L-R)(CO)2Cl2] complexes efficiently catalyze cross-coupling of arylaldehydes with arylboronic acids yielding diaryl ketones.

-

Hurd,Jones,Blunck

, p. 2033,2035 (1935)

-

Clean and efficient benzylic C-H oxidation using a microflow system

Lv, Xiao-Ming,Kong, Ling-Jie,Lin, Qi,Liu, Xiao-Feng,Zhou, Ya-Ming,Jia, Yu

, p. 3215 - 3222 (2011)

An efficient procedure using microreactors for the oxidation of benzylic compounds is described. This new method is facile, economical, and environmentally friendly. By using microreactors, this oxidation can be accomplished with good yields within 10s at room temperature. Copyright

Direct Thioepoxidation of Strained Cyclic Alkenes by the Photolytic Sulfur-Atom Transfer from Thiocarbonyl S-Oxides (Sulfines)

Adam, Waldemar,Deeg, Oliver,Weinkoetz, Stephan

, p. 7084 - 7085 (1997)

-

Reactions in Dry Media: Oxidative Cleavage of Olefins Adsorbed on Inorganic Supports with Oxygen

Aronovitch, Chaim,Mazur, Yehuda

, p. 149 - 150 (1985)

Substituted phenylethylenes adsorbed on inorganic supports are oxidatively cleaved to ketones or aldehydes under illumination in the presence of oxygen.It is suggested that these oxidations invove the intermediacy of cation radicals whose formation is initiated by contact charge-transfer interactions between the olefins on the adsorbing phase and oxygen molecules.

-

Borch,R.F. et al.

, p. 726 - 729 (1972)

-

Alkyl Hydroperoxide Oxidation of Alkanes and Alkenes with a Highly Active Mn Catalyst

Sarneski, Joseph E.,Michos, Demetrius,Thorp, H. Holden,Didiuk, Mary,Poon, Thomas,et al.

, p. 1153 - 1156 (1991)

The system ROOH/(ClO4)4 hydroxylates alkanes and converts ArCR=CH2 to ArCR=O with extremely high activity and good conversions and yields.

Deuterium kinetic isotope effects in homogeneous decatungstate catalyzed photooxygenation of 1,1-diphenylethane and 9-methyl-9H-fluorene: Evidence for a hydrogen abstraction mechanism

Lykakis, Ioannis N.,Orfanopoulos, Michael

, p. 7835 - 7839 (2005)

The homogeneous decatungstate W10O324- catalyzed photooxygenation of 1,1-diphenylethane and 9-methyl-9H-fluorene has been studied mechanistically. The primary and β-secondary kinetic isotope effects provide strong evidence for a stepwise mechanism, with a hydrogen atom abstraction in the rate-determining step.

Formation of an Ozonide by Electron-Transfer Photooxygenation of Tetraphenyloxirane. Cosensitization by 9,10-Dicyanoanthracene and Biphenyl

Schaap, A. Paul,Lopez, Luigi,Gagnon, Steven D.

, p. 663 - 664 (1983)

-

-

Kekule,Franchimont

, p. 908 (1872)

-

Structural Effects of Olefins in the Photooxygenation with Electron-Accepting Sensitizers. Kinetic Approach to Reactive Intermediates

Konuma, Satoshi,Aihara, Shin,Kuriyama, Yasunao,Misawa, Hiroaki,Akaba, Ryoichi,et al.

, p. 1897 - 1900 (1991)

Pulsed laser excitation studies on the reactive species in 9-cyanoanthracene(CNA)-sensitized oxygenation of 1,1-diphenyl-2-methylpropene (1a) and (E)-2,3-diphenyl-2-butene (1b) show that the reaction course is mostly governed by competitive quenching of the CNA excited singlet by 1 and oxygen to produce 1+. and 1O2, respectively.The results indicate that the reaction courses of tetraphenylethylene and 2,3-dimethyl-2-butene, for example, can be explaind by exclusive quenching of sensitizer singlets by the olefin and oxygen, respectively.

Chromium-Mediated Benzylic Oxidations by Sodium Percarbonate in the Presence of a Phase Transfer Catalyst.

Muzart, Jacques,Aiet-Mohand, Samia

, p. 5735 - 5736 (1995)

In the presence of catalytic amounts of (n-Bu3SnO)2CrO2, Adogen 464 and p-toluenesulfonic acid, benzylic methylene groups are effectively oxidized into alcohols and ketones by sodium percarbonate in refluxing acetonitrile.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

Niu, Kaikai,Shi, Xiaodi,Ding, Ling,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin

, (2021/12/13)

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.

Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage

Ma, Yangmin,Shao, Lei,Szostak, Michal,Wang, Ruihong,Zhang, Jin,Zhang, Pei

supporting information, (2022/01/04)

Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe

Radical Alkene-Trifluoromethylation-Triggered Nitrile Insertion/Remote Functionalization Relay Processes: Diverse Synthesis of Trifluoromethylated Azaheterocycles Enabled by Copper Catalysis

Li, Wen-Cheng,Liao, Wei-Wei,Sun, Yun-Hai,Wei, Zhong-Lin,Wu, Yu-Heng,Xi, Ji-Ming

supporting information, p. 1110 - 1115 (2022/02/10)

A copper-catalyzed alkene-trifluoromethylation-triggered nitrile insertion/remote functionalization relay process has been achieved, in which "interrupted"remote 1,n-difunctionalizations of alkenes with nitrile insertion can deliver iminyl radical interme

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Ou, Jinhua,Tan, Hong,He, Saiyu,Wang, Wei,Hu, Bonian,Yu, Gang,Liu, Kaijian

, p. 14974 - 14982 (2021/10/25)

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Microwave Assisted Oxidation of Benzyl Halides to Aldehydes and Ketones with 4-Hydroxypyridinium Nitrate Functionalized Silica Gel in Aqueous Media

Ghalehbandi, Shermineh sadat,Ghazanfari, Dadkhoda,Ahmadi, Sayed Ali,Sheikhhosseini, Enayatollah

, p. 176 - 183 (2021/04/29)

-

Process route upstream and downstream products

Process route

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

benzophenone
119-61-9

benzophenone

tert-butylamine hydrochloride
10017-37-5

tert-butylamine hydrochloride

Conditions
Conditions Yield
With N,N-dichloro-t-butylamine; In tetrachloromethane; at 20 ℃; for 1h; Product distribution; Irradiation;
98 % Chromat.
90%
2,2-diphenyl-1,3-oxathiolane
33735-40-9

2,2-diphenyl-1,3-oxathiolane

2-carboxybenzene diazonium chloride
4661-46-5

2-carboxybenzene diazonium chloride

benzophenone
119-61-9

benzophenone

phenylthioethylene
1822-73-7

phenylthioethylene

Conditions
Conditions Yield
With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Mechanism; Heating;
67%
82%
With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Heating;
82%
67%
1-(diphenylmethyl)-4-nitrobenzene
2945-12-2

1-(diphenylmethyl)-4-nitrobenzene

benzophenone
119-61-9

benzophenone

Conditions
Conditions Yield
With potassium hydroxide; oxygen; In 1,2-dimethoxyethane; at 20 ℃; for 0.5h;
30%
35%
C<sub>23</sub>H<sub>16</sub>N<sub>2</sub>O<sub>2</sub>
115993-91-4

C23H16N2O2

4-chloroquinoline
611-35-8

4-chloroquinoline

benzophenone
119-61-9

benzophenone

hexachloroethane
67-72-1

hexachloroethane

benzophenone azine
983-79-9

benzophenone azine

Conditions
Conditions Yield
With tetrachloromethane; Yields of byproduct given; Ambient temperature; Irradiation;
80%
(2-Diethylamino-ethylamino)-diphenyl-methanol
80500-15-8

(2-Diethylamino-ethylamino)-diphenyl-methanol

benzophenone
119-61-9

benzophenone

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

Conditions
Conditions Yield
With water; In acetonitrile; at 30 ℃; Rate constant;
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

acetophenone
98-86-2

acetophenone

benzophenone
119-61-9

benzophenone

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

Conditions
Conditions Yield
With potassium hydroxide; carbonylbis(trifluoroacetato)bis(triphenylphosphine)ruthenium; at 140 ℃; for 0.2h; Equilibrium constant; Thermodynamic data; ΔG (gas);
potassium hydroxide; Ru(CF3CO2)CO(PPh3)2; at 140 ℃; for 12h; Equilibrium constant; Rate constant; variat. KOH concentration;
benzophenone-α-cyclodextrin

benzophenone-α-cyclodextrin

benzophenone
119-61-9

benzophenone

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

Conditions
Conditions Yield
In water; at 19.9 ℃; Equilibrium constant;
1-oxo-3,3-diphenyl-phthalan-5-carboxylic acid

1-oxo-3,3-diphenyl-phthalan-5-carboxylic acid

benzophenone
119-61-9

benzophenone

terephthalic acid
100-21-0

terephthalic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
beim Schmelzen;
α,α-dibromodiphenylmethane
6425-27-0

α,α-dibromodiphenylmethane

water
7732-18-5

water

benzophenone
119-61-9

benzophenone

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
at 150 ℃;
benzhydrylidene-[1]naphthyl-amine
32566-86-2

benzhydrylidene-[1]naphthyl-amine

benzophenone
119-61-9

benzophenone

1-amino-naphthalene
134-32-7

1-amino-naphthalene

Conditions
Conditions Yield

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