50600-30-1

Upstream product

• 22440-35-3 trans-2-(4-methylbenzenyl)-3-phenyl-oxirane 
• 104-87-0 4-methyl-benzaldehyde 
• 948-55-0 1-phenyl-1-p-tolyl-ethylene 
• 80909-79-1 2-(4-methylphenyl)-2-phenyloxirane 
• 32569-84-9 ethoxyethynylbenzene 
• 1207201-96-4 1-(2-methoxy-1-p-tolylvinyl)benzene 
• 6749-78-6 4-methylphenylmagnesium iodide 
• 197230-95-8 N,N-dimethyl-2-[2-(phenyl)ethenyloxy]ethanamine 
• 591-50-4 iodobenzene 
• 4714-21-0 4-methylstilbene 
• 7664-93-9 sulfuric acid 
• 50600-29-8 phenyl-2-p-tolyl-ethane-1,2-diol 
• 22440-35-3 2-phenyl-3-p-tolyl-oxirane 
• 129944-28-1 3-(4-Methylphenyl)-1,1,3-triphenylpropene 

Downstream Products

• 108-88-3 toluene 
• 71-43-2 benzene 
• 890654-72-5 3-(4-methylphenyl)-3-phenylprop-1-ene-1,1-dicarbonitrile 
• 1882-56-0 2-(4-methylphenyl)-2-phenylacetic acid 

Relevant academic research and scientific papers

Regioselective and stereoselective entry to β,β-disubstituted vinyl ethers via the sequential hydroboration/Suzuki-Miyaura coupling of ynol ethers

A highly regio- and stereoselective synthesis of stereodefined β,β-disubstituted alkenyl ethers featuring the sequential hydroboration/Suzuki-Miyaura coupling of ynol ethers has been described. A number of functional groups, including OMe, Ac, CO2Et, CN, halides, and alkyl, (hetero)aryl, and alkenyl groups, are well-tolerated under the reaction conditions. Furthermore, it allows a facile entry to the labile diarylacetaldehydes by TFA-mediated hydrolysis of β,β-disubstituted vinyl ethers.

Rhenium complex-catalyzed Meinwald rearrangement reactions of oxiranes

The Meinwald rearrangement reaction of oxiranes to the corresponding carbonyl compounds is efficiently catalyzed by the ReBr(CO)5 complex.

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Br?nsted-acidic ionic liquids (ILs), and IL/microwave; Experimental and computational substituent effect study on aryl versus hydrogen migration

The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF 4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf 2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3 equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5 mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Br?nsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Br?nsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration

The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Br?nsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).

Synthesis of enol ethers and enamines by Pd-catalyzed tosylhydrazide- promoted cross-coupling reactions

"Chemical Equation Presented" α-Substitution is fine: α-Alkoxycarbonyl and α-aminocarbonyl compounds are good substrates for the recently developed tosylhydrazide-promoted Pd-catalyzed cross-coupling of carbonyls with aryl halides. The reac-tion gives ris

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

Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a heck triarylation process

This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled tri- and diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.

Selective isomerization of aryl substituted epoxides to aldehydes via iron Lewis acid catalysis

The iron Lewis acid [(η5-C5H5)Fe(CO)2(THF)]+BF4- (2) catalyzes the ring opening isomerization of aryl substituted epoxides (1) to aldehydes (3) in excellent yield.

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.