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Cas Database

486-25-9

486-25-9

Identification

  • Product Name:9-Fluorenone

  • CAS Number: 486-25-9

  • EINECS:207-630-7

  • Molecular Weight:180.206

  • Molecular Formula: C13H8O

  • HS Code:29143900

  • Mol File:486-25-9.mol

Synonyms:Fluoren-9-one(8CI);Fluorenone;NSC 5181;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:No signal word.

  • Hazard Statement:H411 Toxic 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 If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • 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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  • Manufacture/Brand:TRC
  • Product Description:9-Fluorenone
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  • Product Description:9-Fluorenone >98.0%(GC)
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Relevant articles and documentsAll total 629 Articles be found

Lobanova, I. A.,Zdanovich, V. I.,Petrovskii, P. V.,Vasyukova, N. I.,Kolobova, N. E.

, (1987)

Davis et al.

, p. 2264 (1969)

Denney,Klemchuk

, p. 6014 (1958)

Richardson,Hodge

, p. 1216 (1970)

Fulvalene Derivatives Containing a Tetrabenzofluorene Unit: New Nonplanar Fulvalenes with High Electron Affinity

Yamada, Kenta,Shibamoto, Hiroshi,Tanigawa, Yusuke,Ishikawa, Hiroyuki,Nishida, Jun-Ichi,Kitamura, Chitoshi,Kurata, Hiroyuki,Kawase, Takeshi

, p. 2085 - 2090 (2016)

17H-Tetrabenzo[a,c,g,i]fluoren-17-one possessing a nonplanar, helicene-like structure was efficiently prepared by aerial oxidation of 17H-tetrabenzo[a,c,g,i]fluorene under mild basic conditions. A quinone methide and an unsymmetrical fulvalene containing a tetrabenzofluorene unit were synthesized from the ketone. Treatment of 17-bromotetrabenzo[a,c,g,i]fluorene with a base afforded a symmetric fulvalene as an air-sensitive blue solid. Electrochemical analyses revealed that these compounds have high electron affinities.

Ghera et al.

, p. 3627,3628, 3630 (1976)

Lobanova, I. A.,Batsanov, A. S.,Zdanovich, V. I.,Struchkov, Yu. T.,Kolobova, N. E.

, (1988)

A novel method for monitoring the transesterification reaction of oil in biodiesel production by estimation of glycerol

Reddy, Sabbasani Rajasekhara,Titu, Devamani,Chadha, Anju

, p. 747 - 754 (2010)

A quantitative method is reported for the estimation of glycerol during transesterification of oil to form biodiesel. The reagent used to derivatize glycerol was 9,9-dimethoxyfluorene. Glycerol is estimated by both UV-visible spectrophotometric and high performance liquid chromatography methods. Using the former method, detection limits of 0.05% w/w of glycerol in biodiesel was established. Validation of the developed method was done using the Greenhill method for determination of free glycerol formed during the transesterification reaction.

-

Schiessler,Eldred

, p. 3958 (1948)

-

-

Schoenberg,Awad

, p. 788 (1950)

-

Chromium-assisted oxidations with sodium perborate by phase transfer catalysis

Muzart,N'Ait Ajjou

, p. 575 - 580 (1991)

Oxidation by sodium perborate of selected alcohols and unsaturated compounds to ketones and acids was achieved at 60-80°C in the presence of catalytic amounts of chromium(VI) oxide and methyltridecylammonium chloride.

Synthesis of fluorovinyl pyrazolyl (thio)ethers by the reaction of gem-difluoroalkenes with pyrazolin-5-ones (thiones)

Huang, Tao,Zhao, Xianghu,Ji, Xinfei,Wu, Wei,Cao, Song

, p. 61 - 68 (2016)

A mild and efficient method for the preparation of fluorovinyl pyrazolyl ethers and thioethers by the reaction of gem-difluoroalkenes having aryl substituents with pyrazolin-5-ones and pyrazolin-5-thiones, respectively, in the presence of t-BuOK is described.

Retro Abramov vs. Rearrangement path competition in hydroxyphosphonate decomposition

Gancarz, Roman,Gancarz, Irena,Deron, Agnieszka

, p. 61 - 69 (2000)

1-hydoxyphosphonates in the presence of aliphatic amine undergo two competitive processes: retro Abramov reaction and intramolecular hydroxyphosphonate-phosphate rearrangement. Both reaction rates and their ratio strongly depend on the nature of the substituent on a alpha carbon atom. Kinetic experiments indicate that two reactions proceed via common transition state.

Ruthenium-catalyzed cytochrome P-450 type oxidation of alkanes with alkyl hydroperoxides

Murahashi,Oda,Naota,Kuwabara

, p. 1299 - 1302 (1993)

The ruthenium-catalyzed oxidation of alkanes with t-butyl hydroperoxide under mild conditions gives the corresponding ketones and alcohols highly efficiently. Kinetic study revealed that the reaction involves hydrogen abstraction of oxoruthenium species.

-

Wade et al.

, p. 3724 (1979)

-

Tetracyclic arenes by benzannulation of tricyclic carbene complexes of chromium with alkynes: Chemo-, regio-, and stereoselectivity

Pfeiffer, Juergen,Nieger, Martin,Doetz, Karl Heinz

, p. 1843 - 1857 (1998)

The tricarbonyl chromium complexes 7-9 and the tetracyclic arenes 11-13 were synthesized from 1-hexyne and the tricyclic chromium carbene complexes 3-5, which are derived from diazo precursors. The nonplanar dibenzocycloheptenylidene complex 4 afforded the benzannulation product S(p)M(h)/R(p)P(h)-8 stereoselectively, as established by NMR spectra and an X-ray crystal structure analysis. The benzannulation failed with the carbene complexes 1 and 2, presumably due to their reduced propensity for decarbonylation. Upon reaction with 1-hexyne, carbene complex 21, bearing two electronically different arene substituents, revealed only a low regioselectivity (1.6:1) in favour of chromium complex 22, which results from the annulation of the less electron-rich arene ring.

-

Huntress,Hershberg,Cliff

, p. 2720,2724 (1931)

-

Substituent and pH Effects on the Hydrolysis Modes of 9-(dinitromethyl)-9-alkoxylfluorenes

Hoz, Shmaryahu,Perach, Sara Sima

, p. 4056 - 4059 (1982)

The hydrolysis of 9-(dinitromethyl)-9-alkoxyfluorene was studied in aqueous solution over the pH range 3-12.Under acidic conditions, the reactions proceed via the fluorenyl oxocarbonium ion in analogy with ketal hydrolysis reactions.Rate constants for the neutral adducts decrease in the order 2-Pr > 2-Et > 2-Me >> 2-Tf.This order of reactivity indicates that substituent electronic effects dominate, whereas steric affects are only of secondary importance.Comparison with literature data for ketal hydrolysis reactions indicates the general validity of this conclusion for the above class of reactions.Out of the four substrates only 2-Tf undergoes hydrolysis under basis conditions by an E1cB mechanism.The other three adducts are practically inert under basic conditions (pH>9).The pKa's of the four substrates range from 6.3 to 6.7, indicating again a small or constant sensitivity to the steric size of the substituent.

On the mechanism of the directed ortho and remote metalation reactions of N,N-dialkylbiphenyl 2-carboxamides

Tilly, David,Fu, Jian-Min,Zhao, Bao-Ping,Alessi, Manlio,Castanet, Anne-Sophie,Snieckus, Victor,Mortier, Jacques

, p. 68 - 71 (2010)

"Chemical Equation Presented" A study concerning the mechanism of the LDA-mediated ortho and remote metalation of N,N-dialkyl-2-biphenyl carboxamides (e.g., 4a) is reported. On the basis of site-selective lithiation/electrophile quench experiments, including deuteration, the LDA metalation of 4 is proposed to involve initial amide-base complexation (CIPE) and equilibrium formation of 5, whose fast reaction with an in situ electrophile (TMSCI) to afford 6 prevents its equilibration with 7. In the absence of an electrophile,5 undergoes equilibration via 4a with 7, whose fate is instantaneous cyclization to a stable tetrahedral carbinolamine oxide 8 which, only upon hydrolysis, affords fluorenone (3).

-

Metz

, p. 612 (1972)

-

C-OH bond cleavage initiated by electron transfer: Electroreduction of 9-fluorenol

Mendkovich, Andrey S.,Syroeshkin, Mikhail A.,Nasybullina, Darya V.,Mikhailov, Mikhail N.,Gultyai, Vadim P.,Elinson, Mikhail N.,Rusakov, Alexander I.

, p. 962 - 973 (2016)

Cyclic voltammetry, chronoamperometry, coulometry, electrolysis, digital simulation, quantum chemical calculations of 9-fluorenol as an example, were used to show that the electroreduction of aryl derivatives of methanol in 0.1 M Bu4NClO4/DMF proceeds via the ECE mechanism (including the stages of radical anion formation and the C-OH bond cleavage in the radical anion) complicated by the reactions of the depolarizer with the anionic products. Among these reactions are the deprotonation of 9-fluorenol and its monoanions by hydroxide anion and fluorenyl anion. The thermodynamic parameters of the reactions have been estimated both theoretically and experimentally. It was found that the equilibrium constants of the fluorenyl anions deprotonation are close (C-anion) or higher (O-anion) than that of fluorenol. As a result the total equilibrium is shifted towards the side of the dianion of 9-fluorenone. The unusual ratio of the equilibrium constants was explained by lower basicity of π?-dianion compare with other anions.

Novel photo-induced coupling reaction of 9-fluorenylidenemalononitrile with 10-methyl-9,10-dihydroacridine

Jiang, Hong,Liu, You-Cheng,Li, Jing,Wang, Guan-Wu,Wu, Yun-Dong,Wang, Quan-Ming,Mak, Thomas C. W.

, p. 882 - 883 (2002)

9-Fluorenylidenemalononitrile reacts with 10-methyl-9,10-dihydroacridine in deaerated acetonitrile under irradiation with λ > 320 nm to give a coupling product 9-dicyanomethyl-9-(10′-methyl-9′-acridinyl)fluorene, characterized by X-ray crystallographic, MS and NMR analyses.

Selective Oxidation of Arenes in Dry Media under Focused Microwaves

Oussaid, Abdelouahad,Loupy, Andre

, p. 342 - 343 (1997)

Arenes are oxidized into ketones within 10-30 min using KMnO4 impregnated on alumina under microwave activation in dry media, instead of several days under classical conditions.

Different Z/E-selectivity depending upon the length of the acyl side chain in the formation of 2,2′-diacyl-9,9′-bifluorenylidene

Oota, Atsushi,Imai, Toshinobu,Yamazaki, Ayumi,Oba, Toru,Karikomi, Michinori,Minabe, Masahiro

, p. 333 - 335 (2006)

We studied the formation of 2,2′-diacyl-9,9′-bifluorenylidene from 2-acyl-9-bromofluorene via the corresponding intermediate 9-bromo-9,9′-bifluorenyl. It was found that dehydrobromination of the 9-bromo-9,9′-bifluorenyl derivatives occurred through the E2 elimination sequence, suggesting that the configuration of 9-bromo-9,9′-bifluorenyl isomers determined the stereochemistry of the product. Facile isomerization of the formed 9,90-bifluorenylidenes may give the observed stereo-selectivity depending upon the length of the acyl side chain.

Huurdeman et al.

, p. 3449 (1971)

Yang,Johnson

, p. 3754 (1977)

Oxidative carbonylation of aromatic hydrocarbons in the system containing Pd or Rh compound, trifluoroacetic acid and its anhydride, and MnO2 or Mn2O3

Kalinovskii,Pogorelov,Gelbshtein,Akhmetov

, p. 1457 - 1462 (2001)

Manganese(II) and manganese(IV) oxides are effective oxidants for the reaction of oxidative carbonylation of aromatic hydrocarbons proceeding at 0.1-1.5 MPa of CO and 20-100°C in trifluoroacetic acid and its anhydride and catalysed by Pd and Rh compounds. Under these conditions up to 9000 moles of aromatic acid is formed per 1 g-at of platinum. With rhodium catalyst instead of the palladium in the case of toluene content of p-toluic acid in the target product increases from 50 to 90%. Carbonylation of biphenyl at 0.1 MPa of CO and 20°C leads toformation of about 15% of fluorenone together with 4-phenylbenzoic acid (60%).

Evidence for rhenaphenanthrene formation and its conversion to fluorenone

Mike, Carl A.,Ferede, Roman,Allison, Neil T.

, p. 1457 - 1459 (1988)

Introduction of 2,2′-dilithiobiphenyl to PPh3(CO)4ReBr gives 9-fluorenone. 9-Fluorenone may be formed via a reductive elimination from a rhenaphenanthrene intermediate. Reaction of 2,2′-dilithiobiphenyl with (CO)5ReBr also gives 9-fluorenone. A mechanism consistent with this conversion involves formation of a rhenacycloheptatetraene followed by ring contraction to the rhenaphenanthrene 4. Reductive elimination from 3 gives the product. Reaction of 2,2′-dilithiobiphenyl with (CO)5ReBr followed by low-temperature oxidative quenching generates 9,10-phenanthrenequinone and 9-fluorenone. Isolation of 9,10-phenanthrenequinone supports the mechanistic route that incorporates the rhenacycloheptatetraene intermediate.

Surface-inspired molecular vanadium oxide catalysts for the oxidative dehydrogenation of alcohols: Evidence for metal cooperation and peroxide intermediates

Werncke, C. Gunnar,Limberg, Christian,Knispel, Christina,Mebs, Stefan

, p. 12129 - 12135 (2011)

On the basis that thiacalix[4]arene (H4T4A) complex (PPh 4)2[H2T4A(VO2)]2 (Ia) was found to be an adequate functional model for surface species occurring on vanadium oxide based catalysts and itself catalyses the oxidative dehydrogenation (ODH) of alcohols, an analogue containing 2,2′-thiobis(2, 4-di-tert-butylphenolate), SL2-, as ligand, namely, (PPh4)2[SLVO2]2 (II) was investigated in the same context. Despite the apparent similarity of Ia and II, studies on II revealed several novel insights, which are also valuable in connection with surfaces of vanadia catalysts: 1) For Ia and II similar turnover numbers (TONs) were found for the ODH of activated alcohols, which indicates that the additional OH units inherent to Ia do not contribute particularly to the activity of this complex, for instance, through prebinding of the alcohol. 2) On dissolution II enters into an equilibrium with a monomeric form, which is the predominant species in solution; nevertheless, ODH proceeds exclusively at the dimeric form, and this stresses the need for cooperation of two vanadium centres. 3) By omitting O2 from the system during the oxidation of 9-fluorenol, the reduced form of the catalyst could be isolated and fully characterised (including single-crystal X-ray analysis). The corresponding intermediate had been elusive in case of thiacalixarene system Ia. 4) Reoxidation was found to proceed via a peroxide intermediate that also oxidises one alcohol equivalent. As the peroxide can also perform mono- and dioxygenation of the thioether group in II, after a number of turnovers the active catalyst contains a sulfone group. The reduced form of this ultimate catalyst was also isolated and structurally characterised. Possible implications of 1)-4) for the function of heterogeneous vanadia catalysts are discussed.

CeO2–δ-Modified CuFe2O4 with Enhanced Oxygen Transfer as Efficient Catalysts for Selective Oxidation of Fluorene under Mild Conditions

Huang, Xiubing,Wang, Peng,Zhang, Hean,Guo, Zhengwei,Liu, Jijia,Lu, Guilong,Pang, Guangsheng,Wang, Ge

, p. 91 - 97 (2019)

The design of efficient catalysts for the selective oxidation of sp3 C–H bond with air at low temperature is of great importance to the scientific and industrial community. In this work, we design a CeO2–δ modified CuFe2O4 catalyst by a post-modification method for the selective oxidation of fluorene under an air atmosphere and N-hydroxyphthalimide (NHPI) at 60 °C. HRTEM results indicate that CeO2–δ nanoclusters sized around 5 nm are successfully modified on the surface of CuFe2O4. XPS and H2-TPR results show that CeO2–δ modification would favor oxygen transfer at lower temperature due to the synergetic effect between CuFe2O4 and CeO2–δ with rich Ce3+/Ce4+ couples. The results demonstrate that CuFe2O4@CeO2–δ-0.05 with 4.20 wt.-% Ce present the best catalytic performance with 94 % conversion of fluorene and excellent reusability at least five times. It is anticipated that the modification of CeO2–δ nanoclusters on the surface leads to increased oxygen activation and transfer to CuFe2O4, which favors the activation of NHPI to phthalimide-N-oxyl (PINO) radicals and exhibits an improved catalytic performance. Our results provide some guidance on the design of efficient catalysts by the surface modification strategy.

Substitution of 9-(α-bromo-α-arylmethylene)fluorenes by thiolate ions in aqueous acetonitrile

Rappoport, Zvi,Shainyan, Bagrat A.

, p. 871 - 878 (1997)

The substitution of 9-(α-bromo-α-arylmethylene)fluorenes by MeS- and p-TolS- ions in 80% MeCN-20% H2O is a second-order reaction. With MeS- ,for the change of the α-aryl group, Hammett's p=l.07 in MeCN. The reaction rate decreases on increasing the water content of the medium. The reactions proceed by the AdN-£ route and no competitive SN1 reaction was observed. The expected influence of the changes in the substituent, solvent, nucleophile and nucleofuge on the competition between the AdN-E and SN1 reactions was analyzed.

Vitamin B12 supported on graphene oxide: As a bio-based catalyst for selective aerobic oxidation of alcohols

Shaabani, Ahmad,Rashidi Vahid, Adina,Shaabani, Shabnam,Mohammadian, Reza,Nazeri, Mohammad Taghi,Keramati Nejad, Mina

, (2018)

The environmental impact of chemical processes has now opened new windows of opportunity for bio-based catalysts. In this paper a highly active bio-based catalyst of vitamin B12 supported on graphene oxide nanosheets is reported for the selective aerobic oxidation of alcohols to the corresponding carbonyl compounds. Operational simplicity, mild reaction conditions, high yield and selectivity, non-hazardous nature, commercial availability and affordability are the main advantages of this novel catalytic system.

Indolopyridines with a bridging heteroatom. 9. Synthesis, structure, and thermolysis of 5-hydroxy-5-(2-pyridyl)-fluorene and -4-azafluorene

Soldatenkov,Kolyadina,Kuleshova,Khrustalev

, p. 817 - 821 (1996)

Treatment of fluorenone or 4-azafluoren-9-one with 2-pyridyllithium gives 5-hydroxy-5-(2-pyridyl)fluorene and its aza analog. The structure of the former has been studied by x-ray crystallography. It was found that, in contrast to the non-condensed diaryl-2-pyridylcarbinols, these alcohols do not undergo acid catalyzed dehydration and heterocyclization. Under pyrolytic conditions, 5-pyridylfluorenol undergoes fission to form fluorenone. 1997 Plenum Publishing Corporation.

Carbene-to-carbene oxygen atom transfer

Kovacs, Dalila,Lee, Ming-Shi,Olson, David,Jackson, James E.

, p. 8144 - 8145 (1996)

-

Prinzbach,H.,Fischer,U.

, p. 1692 - 1722 (1967)

Pentamethylcyclopentadienyl Half-Sandwich Diazoalkane Complexes of Ruthenium: Preparation and Reactivity

Albertin, Gabriele,Antoniutti, Stefano,Bortoluzzi, Marco,Botter, Alessandra,Castro, Jesús

, p. 5592 - 5602 (2016)

The diazoalkane complexes [Ru(η5-C5Me5)(N2CAr1Ar2){P(OR)3}L]BPh4 (1-4) [R = Me, L = P(OMe)3 (1); R = Et, L = P(OEt)3 (2); R = Me, L = PPh3 (3); R = Et, L = PPh3 (4); Ar1 = Ar2 = Ph (a); Ar1 = Ph, Ar2 = p-tolyl (b); Ar1Ar2 = C12H8 (c); Ar1 = Ph, Ar2 = PhC(O) (d)] and [Ru(η5-C5Me5){N2C(C12H8)}{PPh(OEt)2}(PPh3)]BPh4 (5c) were prepared by allowing chloro-compounds RuCl(η5-C5Me5)[P(OR)3]L to react with the diazoalkane Ar1Ar2CN2 in the presence of NaBPh4. Treatment of complexes 1-4 with H2O afforded 1,2-diazene derivatives [Ru(η5-C5Me5)(η2-NH=NH){P(OR)3}L]BPh4 (6-9) and ketone Ar1Ar2CO. A reaction path involving nucleophilic attack by H2O on the coordinated diazoalkane is proposed and supported by density functional theory calculations. The complexes were characterized spectroscopically (IR and 1H, 31P, 13C, 15N NMR) and by X-ray crystal structure determination of [Ru(η5-C5Me5)(N2CC12H8){P(OEt)3}2]BPh4 (2c) and [Ru(η5-C5Me5)(η2-NH=NH){P(OEt)3}2]BPh4 (7).

Shirafuji et al.

, p. 2249 (1973)

Thermal and photochemical 1,3-dipolar cycloaddition of a sulfine (Fluorenethione S-oxide) to the strained triple bond of cyclooctyne

Adam, Waldemar,Froehling, Bettina,Weinkoetz, Stephan

, p. 9154 - 9155 (1998)

-

Direct proof for a lower reactivity of monomeric vs. dimeric oxidovanadium complexes in alcohol oxidation

Werncke, C. Gunnar,Limberg, Christian,Metzinger, Ramona

, p. 2426 - 2432 (2013)

Previous attempts to synthesize and isolate (thiobisphenolate) vanadium(V) dioxido complexes had always provided their dimers containing [O=V(μ-O) 2V=O]2+ cores, and these also dominate the solution reactivity. Hence, the behavior of their parent monomers, which represent the major species in solution, has remained uncertain. Herein we report the development of a synthetic route that allowed for the successful isolation, spectroscopic investigation, and structural characterization of the monomer PPh4[SLVO2] (3) [SL2- = 2′2-thiobis(2, 4-di-tert-butylphenolate)]. For this purpose PPh 4[SLVOCl2] (1) had to be accessed first in order to convert it to the ethoxido compound PPh4[ SLVO(OEt)2] (2), which is more prone to hydrolysis. Treatment of 2 with stoichiometric amounts of water followed by immediate cooling to -30°C led to crystals of 3. After its dissolution NMR spectra were recorded that were identical with those obtained after dissolution of its dimer, thus confirming the monomer/dimer equilibrium postulated previously. The molecular structure of 3 revealed the absence of a V···S interaction, which, however, stabilizes its dimer, and thus suggested the employment of a bisphenolate ligand lacking a bridging sulfur atom to obtain an analogue, which does not undergo dimerization in solution. In EtL2- the sulfur atom is replaced by an ethylmethine unit and indeed the corresponding complex NBu4[EtLVO 2] (4) proved to be stable as a monomer. Investigation of its potential as a catalyst for the oxidative dehydrogenation of 9-fluorenol confirmed a much lower reactivity in comparison to dimeric complexes, which is discussed. Copyright

Structure of 9-(4-pyridylmethylene)fluorene and 9-(E)-benzylidene-1-azafluorene. Oxidation of 9-(4-pyridylmethylene)fluorene and its condensation with acetylenedicarboxylic acid diester

Kolyadina,Soldatenkov,Gridunova,Prostakov

, p. 833 - 836 (1998)

It war found by x-ray diffraction analysis that in the fulvenes studied, the aromatic rings of the condensed tricyclic fragment are not in the same plane. The angle between them is approximately 4°. The exocyclic carbon atom is at the same angle relative to the plane of the five-membered ring. Starting from 9-(4-pyridylmethylidene)fluorene, there were obtained 3-(4-pyridyl)spirooxirane[2,9′]fluorene and 1,2,3,4-trimethoxycarbonyl-8-(fluorylidene-9-methylene)-9a-H-quinolizine. 1999 Kluwer Academic/Plenum Publishers.

Chardonnens et al.

, p. 3044,3048 (1973)

Dispiro[fluorene-9,5′-[1,2,3,4]tetrathiane-6′, 9″-fluorene]

Linden,Gebert,Heimgartner

, p. 764 - 766 (2001)

The tetrathiane ring of the title compound, C26H16S4, has a chair conformation and the molecule has approximate C2 symmetry. Each of the two fluorene ring systems is virtually planar, with the ring planes intersecting at an angle of 67.58 (5)°. This novel compound has been formed as a side product from the treatment of 9H-fluorene-9-thione with methyl N-[(benzylidene)phenyl]glycinate in the presence of LiBr and 1,6-diazabicyclo[5.4.0]undecane.

Ray,Geiser

, p. 200 (1949)

Denney,Klemchuk

, p. 3285,3287 (1958)

Synthesis of Substituted Quinazolin-4(3H)-imines from Aryldiazonium Salts, Nitriles and 2-Cyanoanilines via A Metal-Free Tandem Approach

Ramanathan, Mani,Liu, Yi-Hung,Peng, Shie-Ming,Liu, Shiuh-Tzung

, p. 5840 - 5843 (2017)

A transition metal-free synthesis of multisubstituted quinazolin-4(3H)-imines has been realized by the direct reaction of aryldiazonium salts, nitriles, and 2-cyanoanilines in a one-pot fashion. This strategy utilizes the in situ formation of reactive N-arylnitrilium intermediate, which undergoes further tandem cyclization with consecutive formation of N-C bonds. Broad functional group compatibility, mild conditions, shorter time, and operational simplicity are the notable features of this report.

Fluorenone Monomer Dianion Studied by 1H and 13C NMR and Charge Density Distribution

Hirayama, Masatoshi,Ohhata, Hiroshi

, p. 2751 - 2756 (1987)

The diamagnetic monomer dianion of fluorenone was prepared from 1,2-dimethoxyethane solution of neutral molecule in contact with excess sodium metal at -5 deg C for 5 days and its 1H and 13C NMR spectra were measured.The possibility that pinacolate-type dimer dianion occurs in an equilibrium system was ruled out from reactivity with oxygen, water, deuterium oxide, and reducible aromatics in addition to the analysis of NMR spectra.The charge density distribution of neutral and dianion molecules was estimated by MO calculations.Comparison between experimental and theoretical 13 C shifts suggested a strong interaction of sodium ions with carbonyl group.It is presumed that an anormalous diamagnetic ring current in 14?-peripheral structure is responsible for poor correlation between theoretical and observed 1H shifts.

Selective Aerobic Oxidation of Csp3-H Bonds Catalyzed by Yeast-Derived Nitrogen, Phosphorus, and Oxygen Codoped Carbon Materials

Ju, Zhao-Yang,Song, Li-Na,Chong, Ming-Ben,Cheng, Dang-Guo,Hou, Yang,Zhang, Xi-Ming,Zhang, Qing-Hua,Ren, Lan-Hui

supporting information, p. 3978 - 3988 (2022/03/16)

Nitrogen, phosphorus, and oxygen codoped carbon catalysts were successfully synthesized using dried yeast powder as a pyrolysis precursor. The yeast-derived heteroatom-doped carbon (yeast@C) catalysts exhibited outstanding performance in the oxidation of Csp3-H bonds to ketones and esters, giving excellent product yields (of up to 98% yield) without organic solvents at low O2pressure (0.1 MPa). The catalytic oxidation protocol exhibited a broad range of substrates (38 examples) with good functional group tolerance, excellent regioselectivity, and synthetic utility. The yeast-derived heteroatom-doped carbon catalysts showed good reusability and stability after recycling six times without any significant loss of activity. Experimental results and DFT calculations proved the important role of N-oxide (N+-O-) on the surface of yeast@C and a reasonable carbon radical mechanism.

Nanostructured Manganese Oxides within a Ring-Shaped Polyoxometalate Exhibiting Unusual Oxidation Catalysis

Sato, Kai,Yonesato, Kentaro,Yatabe, Takafumi,Yamaguchi, Kazuya,Suzuki, Kosuke

supporting information, (2021/12/30)

Nanosized manganese oxides have recently received considerable attention for their synthesis, structures, and potential applications. Although various synthetic methods have been developed, precise synthesis of novel nanostructured manganese oxides are st

PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions

Du, Yunfei,Ouyang, Yaxin,Wang, Xi,Wang, Xiaofan,Yu, Zhenyang,Zhao, Bingyue,Zhao, Kang

, p. 48 - 65 (2021/06/16)

Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.

[Fe(bpy)3]2+-based porous organic polymers with boosted photocatalytic activity for recyclable organic transformations

Liu, Hong-Kun,Lei, Yi-Fei,Tian, Peng-Ju,Wang, Hui,Zhao, Xin,Li, Zhan-Ting,Zhang, Dan-Wei

supporting information, p. 6361 - 6367 (2021/03/22)

Three rigid metal porous organic polymers (POPs) based on an iron(ii) complex are prepared from the condensation reactions of an octahedral [Fe(bpy)3]2+-cored hexaaldehyde and three rod-like aromatic diamines. The POPs have been studied as the first series of earth-abundant metal complex-connected photocatalysts for heterogeneous visible light-driven oxidation of benzyl halides and enantioselective α-alkylation of aldehydes. Both yields and enantioselectivities of the reactions catalyzed by one of the POPs, which possesses the largest porosity, rival or even surpass those of the reactions homogeneously catalyzed by control [Fe(bpy)3]2+complexes. Moreover, POP catalysts are highly stable and exhibit a considerable activity after recycling 10 times.

Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions

Pradhan, Suman,Sharma, Vishali,Chatterjee, Indranil

supporting information, p. 6148 - 6152 (2021/08/03)

A rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.

Process route upstream and downstream products

Process route

9H-fluoren-9-yl bromide
1940-57-4

9H-fluoren-9-yl bromide

C<sub>9</sub>H<sub>7</sub>N<sub>2</sub>O<sub>3</sub><sup>(1-)</sup>*Ag<sup>(1+)</sup>
107985-36-4

C9H7N2O3(1-)*Ag(1+)

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

(Z)-2,3-bis(4-methoxyphenyl)but-2-enedinitrle
4680-92-6

(Z)-2,3-bis(4-methoxyphenyl)but-2-enedinitrle

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

9-fluorenyl(4-methoxyphenyl)(nitro)acetonitrile
107960-28-1

9-fluorenyl(4-methoxyphenyl)(nitro)acetonitrile

Conditions
Conditions Yield
In benzene; for 55h; Ambient temperature;
45%
4.5%
26%
37%
(9-Hydroxy-9H-fluoren-9-yl)-phosphonic acid diisopropyl ester

(9-Hydroxy-9H-fluoren-9-yl)-phosphonic acid diisopropyl ester

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

Conditions
Conditions Yield
With triethylamine; Rate constant; other reagents (n-butyl- and t-butylamine);
9-Benzylidene-9H-fluorene
1836-87-9

9-Benzylidene-9H-fluorene

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With Celite; pyridinium chlorochromate; In dichloromethane; for 28h; Heating; highly selective oxidative cleavage;
85%
86%
With Iron(III) nitrate nonahydrate; oxygen; In dichloromethane; at 150 ℃; for 1h; Microwave irradiation; Sealed tube;
89 %Chromat.
50 %Chromat.
9-Benzylidene-9H-fluorene
1836-87-9

9-Benzylidene-9H-fluorene

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

1-tert-butyl-4-iodobenzene
35779-04-5

1-tert-butyl-4-iodobenzene

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With 4-tButyl iodoxybenzene; In chlorobenzene; at 130 - 140 ℃; for 7h;
45%
92%
50%
C<sub>20</sub>H<sub>15</sub>NO
73311-38-3

C20H15NO

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

benzylidenamine
16118-22-2

benzylidenamine

(E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene
92-29-5,73311-46-3

(E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With DBN; In chloroform-d1; Yield given. Yields of byproduct given;
C-phenyl-N-methylnitrone
3376-23-6,7372-59-0,59862-60-1

C-phenyl-N-methylnitrone

9H-fluorene-9-thione
830-72-8

9H-fluorene-9-thione

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

N-fluorenylidene methylamine N-oxide
33226-81-2

N-fluorenylidene methylamine N-oxide

benzaldehyde
100-52-7

benzaldehyde

2'-methyl-3'-phenylfluorene-9-spiro-4'-(1',2'-thiazolidine)-5'-spiro-9-fluorene
76256-14-9

2'-methyl-3'-phenylfluorene-9-spiro-4'-(1',2'-thiazolidine)-5'-spiro-9-fluorene

Conditions
Conditions Yield
In benzene; for 168h; Further byproducts given; Ambient temperature;
13%
17%
benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

9-diazofluorenone
832-80-4

9-diazofluorenone

9H-fluorene
86-73-7

9H-fluorene

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

9-Benzyloxyfluorene
88655-94-1

9-Benzyloxyfluorene

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
at 10 ℃; for 0.333333h; Yield given. Yields of byproduct given; Irradiation;
C<sub>20</sub>H<sub>15</sub>NO
73311-38-3

C20H15NO

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

(E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene
92-29-5,73311-46-3

(E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
for 12h; Yield given. Yields of byproduct given; Ambient temperature;
Bis-diphenylene-1.3-phenyl-2 allyle-Radikal
256512-13-7

Bis-diphenylene-1.3-phenyl-2 allyle-Radikal

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

9-[(9H-Fluoren-9-ylidene)phenylmethyl]-9H-fluorene
14750-07-3

9-[(9H-Fluoren-9-ylidene)phenylmethyl]-9H-fluorene

9-(fluoren-9-ylidene-phenyl-methyl)-fluoren-9-ol
72087-86-6

9-(fluoren-9-ylidene-phenyl-methyl)-fluoren-9-ol

benzaldehyde
100-52-7

benzaldehyde

9-(Fluoren-9-ylidene-phenyl-methyl)-fluoren-3-one

9-(Fluoren-9-ylidene-phenyl-methyl)-fluoren-3-one

Conditions
Conditions Yield
With oxygen; In toluene; for 12h; Product distribution; Mechanism; Irradiation; when solvent purged with N2 gas, products are different;
41 % Turnov.
10 % Turnov.
32 % Turnov.
2 % Turnov.
8 % Turnov.
C-phenyl-N-methylnitrone
3376-23-6,7372-59-0,59862-60-1

C-phenyl-N-methylnitrone

9H-fluorene-9-thione
830-72-8

9H-fluorene-9-thione

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

N-fluorenylidene methylamine N-oxide
33226-81-2

N-fluorenylidene methylamine N-oxide

benzaldehyde
100-52-7

benzaldehyde

2'-methyl-3'-phenylfluorene-9-spiro-4'-(1',2'-thiazolidine)-5'-spiro-9-fluorene
76256-14-9

2'-methyl-3'-phenylfluorene-9-spiro-4'-(1',2'-thiazolidine)-5'-spiro-9-fluorene

Conditions
Conditions Yield
In benzene; for 168h; Product distribution; Mechanism; Ambient temperature;
17%
13%

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