6954-71-8

Usage

InChI:InChI=1/C20H13NO2/c22-21(23)15-11-9-14(10-12-15)13-20-18-7-3-1-5-16(18)17-6-2-4-8-19(17)20/h1-13H

Upstream product

• 7293-80-3 9-(tributylphosphonio)fluoren-9-ide 
• 555-16-8 4-nitrobenzaldehdye 
• 486-25-9 9-fluorenone 
• 51042-50-3 4-nitrobenzyltriphenylarsonium bromide 
• 7385-10-6 9-(trimethylsilyl)fluorene 
• 7253-07-8 (9H-fluoren-9-yl)triphenylphosphonium bromide 
• 7293-68-7 Tris--fluorenyl-(9)-phosphoniumbromid 
• 124111-83-7 As-(9-fluorenyl)triphenylarsonium bromide 
• 1940-57-4 9H-fluoren-9-yl bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 603-32-7 triphenyl-arsane 
• 82764-10-1 Triphenylarsin-fluorenyliden 
• 6344-52-1 dimethyl (9-fluorenyl)phosphonate 
• 65439-94-3 (4-Nitro-benzylidene)-triphenyl-λ⁵-arsane 

Downstream Products

• 203066-25-5 9-[Bromo-(4-nitro-phenyl)-methylene]-9H-fluorene 
• 6967-16-4 C₂₀H₁₅N 

Relevant academic research and scientific papers

An N-heterocyclic carbene-catalyzed switchable reaction of 9-(trimethylsilyl)fluorene and aldehydes: Chemoselective synthesis of dibenzofulvenes and fluorenyl alcohols

An N-heterocyclic carbene-catalyzed synthesis of dibenzofulvenes and fluorenyl alcohols was developed. In the presence of 10 mol% NHC (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) and 4 ? molecular sieves, 9-(trimethylsilyl)fluorene undergoes an olef

Fulvenyl-Functionalized Polyisocyanides: Cross-Conjugated Electrochromic Polymers with Variable Optical and Electrochemical Properties

We describe the preparation of arylisocyanide monomers bearing conjugated fulvenyl groups derived from 9-benzylidene-9H-fluorene (Flu), 5-benzylidene-1,2,3,4-tetraphenylcyclopentadiene (TPCp), and 5-benzylidene-5H-dibenzo[a,d]cycloheptene (Dbs). The electrochemical and optical properties of the monomers and their precursors have been characterized and consistently showed the effect of the conjugation of the respective functional group (-NO2, -NH2, -NHCHO, and N-C) with the fulvenyl moiety. The isocyanides have been subsequently polymerized to the corresponding polyisocyanides (PICs), which exhibited number-average molecular weights of 124-136 kDa (PDI = 2.0-2.7), as determined by gel permeation chromatography in THF vs polystyrene standards. The thermal, optical, and electrochemical properties of the polymers have been studied in detail. Spectroelectrochemical analyses of polymers equipped with redox-active pentafulvene groups show reversible electrochromism, which allows to lower the optical gap from 2.38 to 1.20 eV (Flu) and from 2.27 to 1.55 eV (TPCp) via chemical or electrochemical reduction.

Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls

The direct palladium-catalyzed intramolecular hydro arylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorpo

Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway

The first example of the palladium-catalyzed exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls has been demonstrated. In contrast to the reported earlier carbocyclizations proceeding via the Friedel-Crafts mechanism, this hydroarylation efficiently proceeds with electron-neutral and electron-deficient arenes, producing fluorene frameworks with defined stereochemistry of the double bond. On the basis of the high reactivity of electron-deficient arenes toward cyclization, high values of inter- and intramolecular kinetic isotope effects, and the exclusive cis-selectivity of cyclization, a mechanism involving a C-H activation motif has been proposed for this transformation. Copyright

Characterization of the Excited-State Reactivity of a Persistent Aryl-Substituted Allyl Free Radical

A family of stable aryl-substituted allyl radicals 1 (9H-fluoren-9-yl-9--9-ylidenephenylmethyls) has been characterized by electronic absorption spectroscopy, semiempirical (AM1) molecular orbital calculations, and cyclic voltammetry.Photolysis of 1a in aerated solvents that are poorer hydrogen atom sources than toluene resulted in oxygenation (ΦOX ca. 5 * 10-4) and cleavage products.A thermally reversible photocyclization mechanism is proposed to explain the oxygenation of 1a in inert solvents.Enhanced excited-state reactivity toward hydrogen and halogen atom donors was observed during the steady-state photolysis of 1a.Electron transfer from naphthalene to an excited state of 1a produces an extremely short lived (30 ps) 1a anion/naphthalene radical cation geminate pair.

Electrochemical reduction of certain fluorenyl and xanthenyl olefins

The reduction of certain fluorene and xanthene containing olefins at a mercury electrode using cyclic voltammetry has been investigated.In DMF, fluorene-9-(4-nitrophenyl)methylene (1) reveals two distinct reversible one-electron redox waves corresponding to anion radical and dianion formation.Some other olefins particularly stilbenes (9-14) and substituted propenones (7,8) show commonality in the emergence of at least one distinct reversible reduction couple.Anion radicals of nearly all of the olefins (1-14) studied in this work generated electrochemically or by chemical 1-electron reductants, exhibited considerable stability.

β-Elimination of the Isonitrile Group in Alkylation Reactions of C-H Acids Activated by the Isonitrile Function

During phase-transfer alkylation of the isonitriles R1R2CHNC with X-CH2-Y, where X is a leaving group and Y an electron withdrawing group, some of the alkylation products undergo β-elimination of the isonitrile function to yield R1R2C=CHY.

Effect of Bulky Size of Carbonyl Systems on Betaine Decomposition of Semi-stablized Arsonium Ylids

Reactions of substituted benzylidentriphenylarsenanes (2a-i) with 9-anthraldehyde and 9-fluorenone have been studied using benzene-sodamide, chloroform-sodium hydride and methanol-sodium ethoxide as solvent-base pairs.In all the cases olefins (5a-i and 6a-i) are formed exclusively.Variation of solvents and bases has no effect on the course of betaine decomposition formed by the nucleophilic attack of ylids on carbonyl systems.

Studies on Betaine Decomposition of Arsonium Ylides

A systematic study on the nature of decomposition of betaine formed by nucleophilic attack of semistabilized arsonium ylides on thiocarbonyl substrates has been carried out.A series of substituted benzylidenetriphenylarsenanes have been generated from their corresponding salts and condensed with few cyclic thioketones to yield exocyclic olefins as exclusive products.The non-availability of thioepoxides indicates that the mode of decomposition of such type of betaines is quite analogous to the betaine formed by phosphonium ylides.The structure of the products have been assigned by IR and NMR spectral studies. - Keywords: Betaine, Arsonium Ylides