13577-28-1

Upstream product

• 25548-89-4 10-methoxy-10-phenyl-9-anthrone 
• 602-55-1 9-phenylanthracene 
• 602-50-6 2-(diphenylmethyl)benzoic acid 
• 1714-15-4 1-phenyl-9-anthrone 
• 67-66-3 chloroform 
• 71-43-2 benzene 
• 613-31-0 9,10-dihydroanthracene 
• 591-50-4 iodobenzene 
• 86901-19-1 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium 
• 120-12-7 anthracene 
• 133744-64-6 rel-(1R,3R,4S)-1,3,4-triphenyl-1,4-dihydrobenzo[d][1,2]oxaphosphinine 3-oxide 
• 126615-78-9 C₂₀H₁₄Mg*3C₄H₈O 
• 108-86-1 bromobenzene 

Downstream Products

• 602-55-1 9-phenylanthracene 
• 5146-30-5 10-phenyl-10-hydroxy-9-anthracenone 
• 14596-70-4 10-phenylanthrone 

Relevant academic research and scientific papers

Cationic polymerization of cis-2,3-tetramethylene-1,4,6-trioxaspiro[4,4] nonane photosensitized by anthracene

A stereoregular poly(ether ester), poly(trans-2-oxycyclohexyl butanoate) (-[trans-2-OCHB]n-) (II), was obtained by cationic polymerization of cis-2,3-tetramethylene-1,4,6-trioxaspiro[4,4]nonane (I) initiated by the 9-phenyl-9,10-dihydroanthrace

Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.

Zinc-Catalyzed Dual C-X and C-H Borylation of Aryl Halides

A zinc-catalyzed combined C-X and C-H borylation of aryl halides using B2pin2 (pin=OCMe2CMe2O) to produce the corresponding 1,2-diborylarenes under mild conditions was developed. Catalytic C-H bond activation occurs ortho to the halide groups if such a site is available or meta to the halide if the ortho position is already substituted. This method thus represents a novel use of a groupXII catalyst for C-H borylation. This transformation does not proceed via a free aryne intermediate, but a radical process seems to be involved. Two B or not two B: A novel catalytic system based on a ZnII-dtbpy precursor was developed for the preparation of 1,2-diborylarenes. This method represents a new type of catalytic process for diborylation of aryl halides via both C-X and C-H activation.

Efficient heterogeneous oxidation of alkylarenes with molecular oxygen

(Chemical Equation Presented) Ru(OH)x/Al2O 3 efficiently catalyzes the heterogeneous aerobic oxygenation or oxidative dehydrogenation of alkylarenes to give the corresponding oxygenated or dehydrogenated products. Catalyst/product separation is very easy, and the recovered catalyst is reusable with retention of the high catalytic performance.

Acidity of dibasic carbon acids. Part 2. Geometry and electronic structure of mono- and di-anions of 9,10-dihydroanthracene and its derivatives in tetrahydrofuran

The geometric-structure, charge distribution and heats of formation of 9-R1-10-R2-9,10-dihydroanthracenes (R1=R2=H;R1=Me, R2=H; R1=R2=Me; R1=Ph, R2/su

The Correct Structure of Cyclic Adducts of (Diphenylmethylene)oxophenylphosphorane witn Aromatic aldehydes

The title cyclic adducts have been reported to be 4-aryl-2,3,3-triphenyl-1,2-oxaphosphetane 2-oxides.However, these compounds are concluded not to be the 1,2-oxaphosphetanes, but 1-aryl-3,4-diphenyl-3,4-dihydro-1H-2,3-benzoxaphosphorin 3-oxides from detailed NMR studies and the investigation of the chemical behavior of the adduct of benzaldehyde.

Magnesium Adducts of Substituted Anthracenes - Preparation and Properties

2-Methyl-, 1,4-dimethyl-, 9-methyl-, 9-ethyl-, 9,10-dimethyl-, and 9-phenylanthracene (1a-f) react with magnesium in THF at room temperature to afford the corresponding substituted magnesium anthracenes 2a-f. 9,10-Diphenylanthracene (1g), however, reacts with magnesium under the same conditions to produce the deep-blue magnesium bis(9,10-diphenylanthracenide) * 6 THF (4g).Upon heating to 60 deg C in THF, 4g reversibly dissociates to give magnesium 9,10-diphenylanthracene * 3 THF (2g) and 1g, while prolonged heating at 60 deg C causes decomposition of 2g to active magnesium (Mg*) and 1g.In THF 2a-c, e, and f exhibit temperature-dependent equilibria with 1a-c, e, and f and magnesium.Compared with magnesium anthracene * 3 THF (2), these equilibria are strongly shifted toward substituted anthracenes and magnesium, and only at 0 deg C high conversions are achieved.The magnesium exchange between 2 and the substituted anthracenes 1a, b, and f in THF has been experimentally verified. 2a, e, and f react with organic halides in the same way as 2, however, in the case of allyl, propargyl, and benzyl chloride the yields of Grignard compounds are lower than for 2; with bromobenzene, the tendency for the radical transfer reaction is stronger than for 2.Magnesium 9,10-dimethylanthracene (2e) reacts with ethyl acetate to give the bicyclic tertiary alcohol 9 by an intramolecular C-C coupling reaction.

Use of Magnesium Anthracene * 3 THF in Synthesis: Generation of Grignard Compounds and Other Reactions with Organic Halides

The course (a), (b), (c) (Scheme 1) of the reaction of magnesium anthracene * 3 THF (1) with organic halides (RX) is dependent on the nature of RX.With alkyl halides in THF 1 reacts as a nucleophile, whereby primary as well as secondary alkyl halides produce dialkyldihydroanthracenes (4-4'') and tertiary alkyl halides yield primarily monoalkyl-substituted dihydroanthracenes (2, 2').With bromo- and iodobenzene in THF 1 reacts predominantly as a radical with H atom abstraction from the solvent affording benzene and 9.The formation of Grignard compounds (5) and anthracene (6), originating from primary and secondary alkyl and aryl halides and 1 in toluene or ether at elevated temperatures, is not caused by the reaction of 1 but by the "active magnesium" (Mg*) formed by decomposition of 1 in these solvents.In contrast, allyl, propargyl, and benzyl halides react with 1 independently of the solvent under mild conditions to produce 5 and 6.Allyl- and the difficultly accessible allenylmagnesium chloride can be prepared in THF at -78 and 0 deg C, respectively, from the corresponding halides and ordinary Mg powder via catalytic amounts of 1.

Hydrogen Transfer between Anthracene Structures

This work reports results of kinetic studies of hydrogen migration between 9,10-dihydro positions in anthracene structures.The transfer of two H atoms from 9,10-dimethyl-9,10-dihydroanthracene (AnH2) to 2-ethylanthracene (EAn) follows simple bimolecular kinetics with k/M-1 s-1=109.64+/-0.14exp (250-375 deg C) At 300-350 deg C, H transfer to 9,10-dimethylanthracene led to nearly equimolar mixtures of cis- and trans-9,10-dihydroanthracene, consistent with a free radical mechanism.The rate-limiting step appears to be transfer of a single benzylic H atom from a donor molecule to an acceptor molecule, resulting in the formation of two highly stabilized free radicals.Reactions of this nature are likely to serve as major sources of free radicals in condensed-phase thermolysis reactions.Measurements of their rate constants offer a new, relatively direct means of determining bond strengths.From the above rate expression, we derive an AnH-H bond strength of 78.4+/- 1.8 kcal mol-1.From literature data for a similar reaction (Halpern et al.) we obtain an H-Mn(CO)5 bond strength of 63 kcal mol-1.Based on an observed lowering of the reaction rate with added anthracene, a rate constant was derived for β-H transfer from a2-ethyl-9-hydroanthryl radical to anthracene.At 350 deg C, this value was 120 M-1 s-1, indicating a high activation barrier (ca. 18 kcal mol-1) for this seldom reported process.