13425-08-6

Upstream product

• 917-64-6 methyl magnesium iodide 
• 14596-70-4 10-phenylanthrone 
• 90292-76-5 2-benzhydryl-benzonitrile 
• 73653-01-7 10-methylanthrone 
• 17407-18-0 9-Methylene-10-ethyl-10-phenyl-9,10-dihydroanthracene 
• 76843-14-6 C₂₁H₁₆O 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 74-88-4 methyl iodide 
• 108-48-5 2,6-dimethylpyridine 
• 3558-69-8 2,6-diphenylpyridine 
• 102477-75-8 9-Hydroxy-9-methyl-10-phenyl-9.10-dihydro-anthracen 
• 56153-60-7 1-(2-chlorophenyl)-1,1-diphenyl methane 
• 108-90-7 chlorobenzene 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 24451-66-9 9-bromomethyl-10-phenyl-anthracene 
• 15012-34-7 9-methyl-10-phenyl-9,10-dihydro-9,10-epidioxido-anthracene 
• 15894-55-0 9,10-Dihydro-9-methyl-9,10-dimethoxy-10-phenyl-anthracen 
• 15674-81-4 9-Aethoxy-9,10-dihydro-10-methylen-9-phenyl-anthracen 
• 25548-89-4 10-methoxy-10-phenyl-9-anthrone 
• 53545-70-3 1,2-bis(10-methyl-9-anthryl)ethane 
• 71339-56-5 9-methoxymethyl-10-phenylanthracene 

Relevant academic research and scientific papers

New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds

A general method for a new, hindered lithium diadamantylamide (LDAM) base-promoted insertion of arynes into Si-P, Si-S, Si-N, and C-C bonds is described. Arynes are generated from easily available aryl triflates and halides. Subsequent reaction of the aryne with silylated phosphines, sulfides, or amines affords the insertion products. Furthermore, a one-step synthesis of anthracenes from aryl halides and aryl ketones is also demonstrated. Cyano, aryl, alkyl, trifluoromethyl, vinyl, methoxy, chloro, fluoro, and even formyl moieties are compatible with the reaction conditions. The new lithium amide affords higher yields compared with lithium tetramethylpiperidide (LiTMP)-promoted reactions. Furthermore, the bulkiness of LDAM base essentially suppresses aryne reaction with base, allowing use of aryl halides and triflates as the limiting reagents.

Flexible and practical synthesis of anthracenes through gold-catalyzed cyclization of o -alkynyldiarylmethanes

A concise gold-catalyzed method for the preparation of anthracenes from o-alkynyldiarylmethanes has been developed. Under mild reaction conditions, versatile anthracene derivatives were formed in moderate to good yields. The high flexibility, broad substrate scope, and mild nature of this reaction render it a viable alternative for the synthesis of anthracenes.

Preparation of benzocyclobutenols by low temperature reaction of ketone enolates with benzynes

The reaction of benzynes, generated from halobenzenes with lithium tetramethylpipiperide (LTMP) at -40 to -78°C, with ketone enolates affords benzocyclobutenols in fair to good yields.

Application of non-steady-state kinetics to resolve the kinetics of proton-transfer reactions between methylarene radical cations and pyridine bases

Apparent deuterium kinetic isotope effects (KIE(app)) of four different methylarene radical cation-pyridine base reactions in dichloromethane (0.2 M tetrabutylammonium hexafluorophosphate) were observed to increase toward a constant value with increasing extent of reaction. The reactions were studied by derivative cyclic voltammetry (DCV), and rate constants were assigned by comparing the experimental with the theoretical DCV data. The kinetic results rule out a simple second-order proton-transfer reaction and implicate a mechanism in which a complex is first formed that then undergoes proton transfer, followed by separation of the products. That KIE(app) are extent of reaction-dependent is observed before steady-state is reached. The concurrent analysis of kinetic data for the reactions of both ArCH3(·+) and ArCD3(·+) with bases under non-steady-state conditions facilitates the resolution of the apparent rate constant [k(app) = k(f)k(p)/(k(b) + k(p))] into the microscopic rate constants (k(f), k(b), and k(p)) for the individual steps. The KIE(app) observed during proton-transfer reactions need not be the real kinetic isotope effects (KIE(real)). Having access to the microscopic rate constants for the steps in which the proton is transferred allows KIE(real) to be evaluated and compared with the corresponding KIE(app). The present study shows that the KIE(real) are much greater than the KIE(app) derived in the usual way from the rate of the overall reaction.

Homolytic Bond Dissociation Energies of the Acidic C-H Bonds in α-Substituted and 10-Substituted 9-Methylanthracenes and Their Related Radical Anions

Equilibrium acidities (pKHA), reduction potentials Ere(HA), oxidation potentials EOX(HA), and oxidation potentials of the conjugate anions EOX(A-) have been measured in dimethyl sulfoxide (DMSO) solution for 13 α-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn).The equilibrium acidities have been shown to be linearly correlated with Hammett ?- constants.The similar ρ- values for the linear correlations of pKHA vs ?- for 9-GCH2An (ρ- = 13.8) and 10-G-9-MeAn (ρ- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities.Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDEHA) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDEHA*-%) of the acidic C-H bonds in 9-GCH2An*- and 10-G-9-MeAn*- radical anions, and (c) the radical cation acidities (pKHA*+%) of the 9-GCH2An*+ and 10-G-9-MeAn*+ radical cations.Introduction of α-CN and α-NO2 groups had opposite effects on the strengths (BDEHA) of the acidic C-H bonds in 9-GCH2An; the α-CN group decreased the BDEHA value by 2.5 kcal/mol and the α-NO2 increased the BDEHA value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An*- radical anions (by 10.6 and 12.5 kcal/mol, respectively).The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol.The 9-GCH2An*+ and 10-G-9-MeAn*+ radical cations are strongly acidic with the pKHA*+% values estimated in the range of -5 to -11 pKHA*+% units.Seven linear free energy relationships have been observed.

Reduction and Thermal Rearrangement of 9-Methylene-10-ethyl-10-phenyl-9,10-dihydroanthracene

The thermolysis of 9-methylene-10-ethyl-10-phenyl-9,10-dihydroanthracene (2) results in a 1,5-ethyl rearrangement to yield 9-propyl-10-phenylanthracene.The rearrangement is shown to occur by an intermolecular radical process.Thermolysis of 2 in thiophenol

CYCLOADDITION OF ARYNES WITH OXAZOLES: A CONVENIENT SYNTHESIS OF VARIOUSLY SUBSTITUTED POLYCYCLIC HYDROCARBONS

Substituted polycyclic ethers and hydrocarbons are synthesised by the cycloaddition reaction of arynes with oxazoles.

Reactions of Copper(II) Halides with Aromatic Compounds. Part XII. Reactions of 9-Methyl-10-phenylanthracene, 1,4,9-Trimethylanthracene, 9,10-Dimethylanthracene and 1,5-Dichloro-9-methylanthracene in Methanol.

The title compounds react with copper(II) bromide in methanol to give the corresponding 9-methoxymethyl compounds. 1,4,9-Trimethylanthracene and 1,5-dichloro-9-methylanthracene also gave 1,2-di-(1,4-dimethyl-9-anthryl)ethane (6) and 1,5-dichloro-9,10-dimethoxy-9,10-dihydroanthracene (9) respectively.The formation of all these products can be interpreted in terms of initial electron transfer oxidation of the substituted anthracene to its radical cation, which either subsequently loses a proton to give the substituted 9-anthrylmethyl radical or undergoes solvent capture.