6000-10-8

Upstream product

• 1692-39-3 (1R,2S)-1,2-bis(4-methoxyphenyl)cyclopropane 
• 2373-89-9 4,4'-dimethoxychalcone 
• 1433968-06-9 1-mesityl-2-((4-methoxybenzyl)thio)-1H-imidazole 
• 1433968-01-4 1-mesityl-2-((4-methoxybenzyl)sulfonyl)-3-methyl-1H-imidazolium trifluoromethanesulfonate 
• 637-69-4 4-Methoxystyrene 
• 1433968-04-7 C₄₈H₆₀AuN₄O₃S⁽¹⁺⁾*CF₃O₃S^(1-) 
• 824-94-2 p-methoxybenzyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 29304-87-8 7-(4-methoxyphenyl)cyclohepta-1,3,5-triene 
• 123-11-5 4-methoxy-benzaldehyde 
• 4705-34-4 1,2-bis(4-methoxyphenyl)ethene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 109423-43-0 C₃₃H₂₆N₂O₂ 
• 109423-43-0 C₃₃H₂₆N₂O₂ 
• 52751-67-4 3,5-bis-(4-methoxyphenyl) isoxazole 
• 20821-99-2 3,5-Bis(p-methoxyphenyl)-4,5-dihydroisoxazole 
• 96908-14-4 4-nitro-3,5-di(p-methoxyphenyl)isoxazole 
• 53629-01-9 erythro-1,2-Bis(p-methoxyphenyl)-1-propanol 
• 53629-01-9 threo-1,2-Bis(p-methoxyphenyl)-1-propanol 
• 76494-78-5 erythro-1,2-Bis(p-methoxyphenyl)-1-methoxypropane 
• 76494-78-5 threo-1,2-Bis(p-methoxyphenyl)-1-methoxypropane 
• 86396-68-1 cis-3,5-bis(4-methoxyphenyl)-1,2-dioxolane 
• 76494-72-9 erythro-1,2-Bis(p-methoxyphenyl)-1-acetoxypropane 
• 76494-72-9 threo-1,2-Bis(p-methoxyphenyl)-1-acetoxypropane 

Relevant academic research and scientific papers

cis-trans Isomerization of 1,2-Bis(4-metoxyphenyl)cyclopropanes via a Cationic Chain Mechanism

Radiation-induced cis-trans isomerization of 1,2-bis(4-metoxyphenyl)cyclopropanes(CP) has been investigated in benzonitrile solution.The isomerization from cis-CP to trans-CP proceeded efficiently ( G = 80 ) via a cationic chain mechanism.Three types of t

Rational design of a gold carbene precursor complex for a catalytic cyclopropanation reaction

Bridging gas- and solution-phase chemistry: A gold(I) carbene precursor complex has been developed and investigated for catalytic cyclopropanation. Formation of the carbene intermediate was first probed by mass spectrometry, followed by cyclopropanation of p-methoxystyrene in solution. The imidazolylidene leaving group serves as a base generated in situ that is necessary in the putative catalytic cycle. Copyright

Cyclopropanation with gold(I) carbenes by retro-Buchner reaction from cycloheptatrienes

Cationic gold(I) promotes the retro-Buchner reaction of 7-substituted 1,3,5-cycloheptatrienes, leading to gold(I) carbenes that cyclopropanate alkenes.

Redox-photosensitized aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia

1,2,4-Triphenylbenzene and 2,2′-methylenedioxy-1,1′ -binaphthalene successfully photosensitized the aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia and primary amines in the presence of m- or p-dicyanobenzene, which gave the 4-amino-1,2-benzocycloalkenes, 3-amino-1-arylpropanes, and 7-amino-5-(p-cyanophenyl)bicyclo[2.2.1]hept-2-ene, respectively. A key pathway for the photosensitized amination is the hole transfer from the cation radicals of the sensitizers that were generated by photoinduced electron transfer to the electron acceptors to the substrates. Therefore, it was found that the relationships in oxidation potentials between the sensitizers and the substrates and the positive charge distribution of the cation radicals of the substrates were important factors for the efficient amination.

Generation of Polyphenylene Radical Cations and Their Cosensitization Ability in the 9,10-Dicyanoanthracene-Sensitized Photochemical Chain Reactions of 1,2-Bis(4-methoxyphenyl)cyclopropane

Cosensitization effects of polyphenylene compounds (PP) such as biphenyl (BP), terphenyls (o-, m-, p-TP), and phenanthrene (Phen) in photoinduced electron-transfer reactions were examined. The 9,10-dicyanoanthracene (DCA)-sensitized cis-trans photoisomerization of 1,2-bis(4-methoxyphenyl)-cyclopropane (CP), which proceeds in a chain reaction via free radical cation of CP (CP.+) as a chain carrier, was accelerated by adding PP, particularly by TP. A similar accelerating effect was observed in the DCA-sensitized photooxygenation of CP as another example. BP and TP were more stable under the oxygenation condition than phenanthrene and naphthalene, which also accelerate the photooxygenation CP. CP.+ is generated by the direct electron transfer from CP to the excited singlet state of DCA (1DCA*) and also by the secondary electron transfer from CP to PP.+, which is generated by the primary electron transfer from PP to 1DCA*. The laser flash photolysis study revealed that the quantum yield for the formation of free CP.+ in the direct electron transfer from CP to 1DCA* (ΦCP.+ ≈ 0.1) was smaller than that in the presence of PP. This is due to the high yield of free PP.+ generation by the primary electron transfer and the efficient secondary electron transfer from CP to PP.+. The secondary electron transfers were found to take place in nearly diffusion-controlled rates (0.9-1.5 × 1010 M-1 s-1). The high yield of PP.+ as free radical ions does not seem to be the sole factor of the cosensitization of PP for the DCA-sensitized photoreactions of CP. The ratio of the quantum yields of the photoreactions to that of the initial CP.+ formation (turnover) also increased by the addition of PP from 3 (isomerization) and 15 (oxygenation) to 32-90 for both reactions. The second-order rate constant for the decay of CP.+ in aerated acetonitrile was decreased by a factor of 0.5-0.8 by the addition of PP. We concluded that the cosensitization effect in the photoreaction involves a π-complex formation between CP.+ and PP assisting the chain reaction as well as initial CP.+ formation.

Synthesis and Properties of Polymer-Supported Cyanoaromatic Compounds

The photoreaction of a styrene/4-tributylstannylmethylstyrene (4:1) copolymer with di- and tetra-cyanoaromatic compounds in benzene-acetonitrile(1:1) gave polymers having cyanoaromatic functions in the side chain.These polymers were soluble in benzene and

Photochemistry of 9,10-Dicyanoanthracene-1,2-Diarylcyclopropane Systems. Photocycloaddition and Photoisomerization

The photochemical reactions of 9,10-dicyanoanthracene (DCA)-1,2-diarylcyclopropane (CP) systems have been investigated.In degassed acetonitrile solution, (4? + 2?) photocycloaddition between DCA and CP occurred to give cis- and trans-2,4-diaryl-1,5-dicyano-6,7:8,9-dibenzobicyclonona-6,8-dienes in a 3:1 ratio in good chemical yields although the quantum yields were not high (Φ = 0.002 - 0.04).This photocycloaddition did not occur in benzene.The DCA-sensitized photoisomerization of trans- and cis-1,2-bis(4-methoxyphenyl)cyclopropanes (1a and 2a) in acetonitrile efficiently occurred to afford a photostationary mixture containing 1a and 2a in a 95:5 ratio.The photoisomerization was remarkably accelerated by bubbling air, by adding metal salts such as Mg(ClO4)2 and LiBF4, and also by aromatic hydrocarbons such as phenanthrene and biphenyl.The quantum yield for the photoisomerization of 2a to 1a exceeded unity, indicating that this photoisomerization involved a chain process.The DCA-sensitized photoisomerisation of optically resolved (-)-1a afforded a racemic mixture of (+)-1a and (-)-1a.These photoreactions are initiated by a one-electron transfer from CP to the excited singlet of DCA.The photocycloaddition proceeds via radical ion pairs in solvent cage and the photoisomerization proceeds via solvent-separated radical cations of CP.

CIS-TRANS PHOTOISOMERIZATION AND PHOTOOXYGENATION OF 1,2-DIARYLCYCLOPROPANES. SALT EFFECTS ON THE PHOTOINDUCED ELECTRON TRANSFER REACTIONS

The efficiencies of the 9,10-dicyanoanthracene (DCA)-sensitized cis-trans photoisomerization and photooxygenation of cis- and trans-1,2-bis(4-methoxyphenyl)cyclopropanes (c-CP and t-CP) in CH3CN were remarkably enhanced by the addition of inorganic salts

1,3-Diarylcyclopropenes: Syntheses and a Facile Ene Dimerisation

1,3-Diphenylcyclopropene (3) and its p,p'-dichloro- (4a) and p,p'-dimethyl-derivatives (4b), together with the 3-deuteriated derivative (1,3-diphenylcyclopropene) (3-d), have been prepared by dehydro- or dedeuterio-bromination of the corresponding bromocyclopropanes (6), (16a), (16b), and (6-d2) with ButOK in THF at -30 deg C, whereas the p,p'-dimethoxy-derivative (4c) has been prepared in THF at -78 deg C by protonation of 1-lithio-2,3-bis(p-methoxyphenyl)cyclopropene (18), generated from 1-bromo-2,3-bis(p-methoxyphenyl)cyclopropene (17).All the cyclopropenes (3), (3-d), and (4a-c) are stable only in solution at -78 deg C, and are characterised by means of 13C n.m.r. at this temperature.At higher temperatures, the cyclopropenes (3), (3-d), and (4a-c) readily dimerise to afford the cyclopropylcyclopropenes (7), (7-d2), and (19a-c) in quantitative yields, according to an ene reaction pathway.The cyclopropene (3) also undergoes an ene reaction with tetracyanoethylene, dibenzoylacetylene, and dimethyl acetylenedicarboxylate to give the adducts (13), (14a), and (14b) in moderate yields.Kinetic measurements have been carried out for the ene dimerisation of (3) (at -58 deg, -50 deg, -40 deg, and -30 deg C), (3-d) (at -40 deg and -30 deg C), and (4b,c) (at -30 deg C) in THF.The highly negative ΔS(excit.) value (-137 J mol-1K-1 at 25 deg C) and the fairly large kH/kD value (3.1 at -40 deg and -30 deg C) obtained for the dimerisation of (3) support a concerted mechanism for this reaction.The dimerisation rate of (3) at -30 deg C decreases with substitution by electron-donating groups in the following order: (3) (k2=19.0E-4mol-1s-1), (4b) (10.9E-4), and (4c) (8.3E-4).

9,10-DICYANOANTHRACENE-SESITIZED PHOTOISOMERIZATION OF 1,2-BIS(4-METHOXYPHENYL)CYCLOPROPANES INVOLVING A CHAIN PROCESS

The photochemical cis-trans isomerization of cis- and trans-1,2-bis(4-methoxyphenyl)cyclopropanes sensitized by 9,10-dicyanoanthracene in aerated acetonitrile solutions proceeds via a chain process in which a cation radical produced from the cyclopropanes