4528-66-9

Upstream product

• 2919-20-2 1,1-di(p-tolyl)ethylene 
• 201230-82-2 carbon monoxide 
• 108-88-3 toluene 
• 22370-76-9 1,1-Aethylendioxy-2,2-di-p-tolylaethan 
• 7647-01-0 hydrogenchloride 
• 93902-67-1 ethyl-(2,2-di-p-tolyl-vinyl)-ether 
• 859777-23-4 1,1-di-p-tolyl-ethane-1,2-diol 
• 104-87-0 4-methyl-benzaldehyde 
• 5173-28-4 1,2-di-p-tolylethane-1,2-diol 
• 75801-34-2 2,3-Di-p-tolyloxirane 
• 129919-74-0 3,3-Bis(4-methylphenyl)-1,1-diphenylpropene 
• 940875-51-4 2-oxo-2-p-tolylethyl pivalate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 18869-29-9 (E)-4,4'-dimethylstilbene 

Downstream Products

• 1588-49-4 4,4'-dimethylstilbene 
• 51490-06-3 1,2-di-p-tolyl-ethanone 
• 20809-78-3 bis-(4-methylphenyl)acetic acid 
• 25451-09-6 2,2-Di-p-tolyl-propane-1,3-diol 
• 3457-48-5 1,2-di(4-methylphenyl)-1,2-ethanedione 
• 674334-53-3 3,3-bis(4-methylphenyl)-1-propene-1,1-dicarbonitrile 
• 159269-38-2 4,4-di(4-tolyl)butanoic acid 
• 528856-89-5 1,1-bis(4-tolyl)-2-iodoethane 
• 528856-88-4 2,2-di-para-toluylethanol 

Relevant academic research and scientific papers

Method for preparing substituted carbonyl compound by catalyzing pinacol rearrangement reaction through molecular sieve

The invention discloses a method for preparing a substituted carbonyl compound by catalyzing pinacol rearrangement reaction through a molecular sieve. The method is characterized in that substituted pinacol as a substrate and toluene as solvent are subjected to a rearrangement reaction for 2-5h under the catalysis of an MCM-41, SBA-15, USY, Beta ZSM-5 or other aluminum-containing H-type acidic molecular sieve, the reaction temperature is 80-110 DEG C, the mass ratio of the substituted pinacol to the toluene to the catalyst is 100: 100: (10-50), the catalyst is filtered out after the reaction is finished, and purifying is performed to obtain a product, namely, the substituted carbonyl compound. Compared with the prior art, the method provided by the invention has the advantages of wide substrate application range, cheap catalyst, easy preparation, stability, no pollution to the environment, recyclability, realization of gram-scale preparation, and high reaction yield.

Silica-supported orthophosphoric acid (OPA/SiO2): preparation, characterization, and evaluation as green reusable catalyst for pinacolic rearrangement

In this paper, we report an easy-to-prepare, cost-effective, efficient, and reusable silica-supported orthophosphoric acid (OPA) catalyst for pinacolic rearrangement. The surface properties of this catalyst were successfully characterized with the help of 31P NMR, TGA, DSC, FT-IR, titration, and microscopy. OPA, hydrogen bonded on the surface, is actually the active species and the reaction seems to occur in the liquid phase embedded in the silica support. As a consequence, the extracting solvent should be chosen with cautious to guarantee the recyclability of the catalyst. As example, pinacol rearrangement reactions were successfully realized with this catalyst and OPA/SiO2 proved to be as efficient as homogeneous orthophosphoric acid to promote the reaction of pinacol derivatives. When using dichloromethane as extracting solvent, OPA/SiO2 can be reuse up to ten times without a significant loss of activity. After ten runs, no physical damage of the catalyst has been observed by microscopy proving its suitability for such application.

α,α-Diarylethylene Glycols as Valuable Precursor for Synthesis of 1,1-Diarylethenes and α,α-Diaryl Acetaldehydes

Towards assembling of diarylmethine unit present in biologically important molecules, we have developed a new Weinreb Amide (WA) based building block derived from glycolic acid. The WA functionality present in this building block permits the sequential addition of various arylmagnesium bromide reagents in a controlled manner that enables assembly of a diarylmethine unit. The developed synthetic route provides easy access to important diarylethenes and α,α-diarylethylene glycols. The synthesized α,α-diarylethylene glycols provide access to synthetically important symmetrical and unsymmetrical α,α-diaryl acetaldehydes as valuable intermediates.

Tandem pinacol coupling-rearrangement of aromatic aldehydes with hydrogen catalyzed by a combination of a platinum complex and a polyoxometalate

Together with a strongly oxidizing polyoxometalate, H5PV 2Mo10O40, PtII(N-(2,6- diisopropylphenyl)pyrazin-2-ylmethanimine)Cl2 forms a combined catalyst that was active in the tandem pinacol coupling-rearrangement of aryl aldehydes to give mostly the corresponding diarylacetaldehyde in high yields using molecular hydrogen as the reducing agent. The Royal Society of Chemistry.

Novel synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones

A two-step synthesis of 1-amino-4-arylnaphthalene-2-carbonitriles from diphenylacetaldehydes and 1,1-diphenylacetones involves condensation of the carbonyl compounds with malonodinitrile and cyclization of the aryl-ylidenemalonodinitriles obtained in conc

Synthesis and structure-activity relationship studies of novel 2-diarylethyl substituted (2-carboxycycloprop-1-yl)glycines as high-affinity group II metabotropic glutamate receptor ligands.

The major excitatory neurotransmitter in the central nervous system, (S)-glutamic acid , activates both ionotropic and metabotropic excitatory amino acid receptors. Its importance in connection to neurological and psychiatric disorders has directed great

One-pot conversion of α-substituted arylacetaldehydes into α-dicarbonyl compounds

α-dicarbonyl compounds 7-12 can be easily prepared by reaction of methylene chloride solutions of several α-substituted arylacetaldehydes 1-6 with a slight excess of tris-(o,p-dibromophenyl) ammoniumyl hexachloro antimonate A.

Mechanism of Dicyanoanthracene-Photosensitized Oxygenation of 1,1,2,2-Tetraarylcyclopropanes and 1,1,3,3-Tetraarylpropenes

1,1,2,2-Tetraphenylcyclopropane (2a) and electron-donor-substituted 1,1-diaryl-2,2-diphenylcyclopropanes 2b-f as well as correspondingly substituted 1,1-diaryl-3,3-diphenylpropenes 5a-e and 3,3-diaryl-1,1-diphenylpropenes 6a-e were irradiated in CCl4 and acetonitrile in the presence of oxygen and various sensitizers.The cyclopropanes as well as the propenes are inert toward singlet oxygen in both solvents.In electron-transfer-induced oxygenation reactions, photosensitized by 9,10-dicyanoanthracene in acetonitrile, cyclopropanes 2d-f, carrying efficient electron-donating 4-methoxyphenyl and 4-phenoxyphenyl groups, yield 1,2-dioxolanes 3d-f exclusively.Cyclopropanes 2b and 2c, which carry less efficient electron-donating 4-methylphenyl groups, give rise to dioxolanes 3b and 3c, respectively, as major products.In addition, allylic hydroperoxides 4b and 4c are formed, which are further oxygenated to benzophenone (10) and the corresponding diaryl ketones 7b and 7c. 1,1,2,2-Tetraphenylcyclopropane (2a) yields dioxolane 3a and allylic hydroperoxide 4a in a ratio of 3:2 as major products; in addition, 1,1,3,3-tetraphenylpropene (5a=6a) is formed as a minor product that is oxygenated under the reaction conditions to benzophenone (10) and diphenylacetaldehyde (8).By use of biphenyl (co-sensitizer), lithium perchlorate (special salt effect), and p-benzoquinone (quencher of O2.-), it is shown that cyclopropanes 2a-f are oxygenated in chain reactions involving (1) 1,3-radical cations 2.+ rather than 1,3-triplet biradicals and (2) triplet ground-state oxygen rather than the superoxide radical anion.Use of 1,8-dihydroxyanthraquinone as a sensitizer supports these results.Propenes 5a-e and 6a-e yield ketones and aldehydes as major products by reactions of 1,2-radical cations 5.+ and 6.+ with O2.- as the oxygenating species.Dioxolanes and allylic hydroperoxides are not produced from these propenes.A mechanism is developed for the electron-transfer-induced photooxygenation of 1,1,2,2-tetraarylcyclopropanes 2 that shows that the increase of the resonance stabilization of the 1,3-radical cation 2.+, caused by substitution of phenyl groups by electron-releasing aryl groups and demonstrated by the concomitantly decreasing oxidation potential of 2, plays the essential role in determining oxygenation rates and product formation.

Superacid-Catalyzed Formylation of Aromatics with Carbon Monoxide

Superacid-catalyzed formylation of aromatics, including benzene, xylenes, mesitylene, and ethylbenzene, with carbon monoxide was investigated.Under comparable reaction conditions, the yield of aromatic aldehydes increases with increasing acidity of the catalyst systems.With CF3SO3H + HF + BF3 and CF3SO3H + SbF5 high yields of aldehydes were obtained under mild conditions even at atmospheric pressure and at 0 deg C.With CF3SO3H + TaF5 and CF3SO3H comparable conversions were only obtained under CO pressure and by using excess acid.In formylation of toluene, in situ further reaction of protonated tolualdehyde with excess toluene gave isomeric ditolylmethanes via the intermediate formation of ditolylmethyl alcohol, together with traces of tritolylmethane.The ditolylmethyl cation formed via ionization of the alcohol reacts with CO to form the corresponding acyl ion, giving subsequently aldehyde or upon aqueous workup some ditolylacetic acid.The amount of these byproducts was 18-20percent for toluene and 3-5percent for xylenes, and none was observed in reaction with mesitylene.Competing acid-catalyzed disproportionation of starting alkylbenzenes led to somewhat more complex reaction mixtures in the case of xylenes and ethylbenzenes.Whereas high positional selectivity was obtained in all systems studied (91-94percent para isomer), the substrate selectivity (kT/kB) varied.With CF3SO3H + HF + BF3 and CF3SO3H + SbF5 it was found lower than in conventional Gatterman-Koch reaction with AlCl3 + HCl or AlCl3 + Cu2Cl2 + HCl and was comparable to that observed in the reaction of HCOF + BF3.Control experiments showed that no decarbonylation of mesitaldehyde and p-tolualdehyde occurs under the reaction conditions.To establish the nature of the electrophilic formylating agent, protolysis of 13C-labeled O-protonated formic acid, H-13C(OH)2+, was studied in CF3SO3H + SbF5 + SO2ClF solution in an attempt to observe the elusive formyl cation at low temperature (-80 deg C) by 13C NMR spectroscopy, but the formyl cation was not observed.Only exchanging 13CO could be detected, suggesting that in the superacid media a rapidly equilibrating protosolvated ion is involved.