58176-63-9

Upstream product

• 39664-98-7 erythro-2-methoxy-1,2-diphenylethylamine 
• 67-56-1 methanol 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 53780-87-3 benzene 
• 100-52-7 benzaldehyde 
• 95607-21-9 2-(2-Methoxy-1,2-diphenyl-ethoxy)-tetrahydro-pyran 
• 1689-71-0 cis-1,2-diphenyloxirane 
• 1439-07-2 trans-Stilbene oxide 
• 1689-71-0 2,3-diphenyloxirane 
• 19455-94-8 (meso-bibenzyldiyl-(α.α'))-sulfite 
• 131829-94-2 1,2-Diphenyl-2-(tetrahydro-pyran-2-yloxy)-ethanol 
• 3524-62-7 benzoin monomethyl ether 

Downstream Products

• 588-59-0 stilbene 
• 1229661-86-2 [(dipicolinate)VO(1,2-diphenyl-2-methoxyethoxide)] 
• 93-58-3 benzoic acid methyl ester 
• 67-56-1 methanol 
• 3524-62-7 benzoin monomethyl ether 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 1263103-05-4 2-(2-methoxy-1,2-diphenylethoxy)pyridine 
• 134-81-6 benzil 
• 24650-42-8 2,2-dimethoxy-2-phenylacetophenone 
• 115889-24-2 (1R,2R)-2-methoxy-1,2-diphenylethan-1-ol 
• 118353-46-1 (1S,2S)-2-methoxy-1,2-diphenylethan-1-ol 
• 94687-10-2 ethyl-3-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propanoate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Relevant academic research and scientific papers

Ionic Pathways in the Photochemistry of Cyclic Sulfite Esters

The photochemistry of cyclic carbonate esters proceeds by the photochemical extrusion of carbon dioxide to give 1, 3-diradicals which produce oxiranes as well as other radical derived species. The corresponding cyclic sulfite esters, upon irradiation, give intermediates that are trapped by alcohols yet generate no oxiranes. These results are consistent with ionic intermediates.

Influence of functionalization of terephthalate linker on the catalytic activity of UiO-66 for epoxide ring opening

A series of five isostructural zirconium terephthalate UiO-66 metal organic frameworks bearing different functional groups on the terephthalate linker (UiO-66-X; X = H, NH2, NO2, Br, Cl,) have been successfully prepared and characterized. UiO-66-X materials were evaluated as heterogeneous catalysts for the epoxide ring opening of styrene oxide by methanol, observing an increase in the initial reaction rate from UiO-66-H to UiO-66-Br, over one order of magnitude. The reactivity order, however, does not follow a linear relationship between the Hammett constant value of the substituent and the initial reaction rate. UiO-66-Br exhibits a wide scope, its activity depending on the structure of epoxide and nucleophile. The absence of Zr leaching to the solution together with the preservation of the UiO-66-X crystallinity confirms the stability of the framework under the reaction conditions. Nevertheless, UiO-66 undergoes a progressive deactivation upon reuse that was attributed to a strong adsorption of the reaction product.

Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides

This paper presents a versatile reagent for epoxide cleavage. The allyltin tribromide could act as a novel and easily prepared allylation reagent and halide atom donor to convert epoxides to the corresponding homoallyl alcohols and halohydrins in high yields with excellent regioselectivities under mild reaction conditions, respectively. It could also act as a Lewis acid to catalyze the ring opening reactions of epoxides with alcohols.

Metal-organic frameworks as efficient heterogeneous catalysts for the regioselective ring opening of epoxides

An iron-based metal-organic framework, [Fe(BTC)] (BTC: 1,3, 5benzenetricarboxylate) is an efficient catalyst in the ring opening of styrene oxide with alcohols and aniline under mild reaction conditions. Out of the various alcohols tested for ring opening of styrene oxide, methanol was found to be the most reactive in terms of percentage conversion and reactivity. The rate of the ring-opening reaction of styrene oxide decreases as the size of the alcohol is increased, suggesting the location of active sites in micropores. [Fe(BTC)] was a truly heterogeneous catalyst and could be reused without loss of activity. The analogous compound [Cu3(BTC)2] was also found to be effective, although with somewhat lower activity than [Fe(BTC)]. The present heterogeneous protocol is compared with a homogeneous catalyst to give an insight into the reaction mechanism.

Pyridine-directed organolithium addition to an enol ether

A previously reported anionic rearrangement of benzyl 2-pyridyl ethers can now be accessed by a distinct and unusual mechanism: addition of alkyllithium reagents to α-(2-pyridyloxy)-styrene triggers an anionic rearrangement to afford tertiary pyridyl carbinols. The process is explained by invoking a contra-electronic, pyridine-directed carbolithiation of the enol ether π-system. Copyright

Novel polymer-supported ruthenium and iron complexes that catalyze the conversion of epoxides into diols or diol mono-ethers: Clean and recyclable catalysts

Polymer-supported metal (Fe or Ru) complexes for epoxide ring opening reactions were successfully prepared by anchoring the bis(2-picolyl)amine ligand onto the polymer poly(chloromethylstyrene-co-divinylbenzene) (PCD); the catalysts showed heterogeneous catalytic activity and easy recyclability in the ring opening reactions of various epoxide substrates with methanol or H 2O at room temperature under mild and neutral conditions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

General asymmetric hydrogenation of α-branched aromatic ketones catalyzed by TolBINAP/DMAPEN-ruthenium(II) complex

(Chemical Equation Presented) A catalyst system consisting of RuCl 2[(S)-tolbinap][(R)-dmapen] and t-C4H9OK in 2-propanol effects asymmetric hydrogenation of arylglyoxal dialkylacetals to give the α-hydroxy acetals in up to 98% ee. Hydrogenation of racemic α-amidopropiophenones under dynamic kinetic resolution predominantly gives the syn alcohols in up to 99% ee and >98% de, while the reaction of racemic bezoin methyl ether gives the anti alcohols in excellent stereoselectivity.

Chemoselective conversion of aromatic epoxide and 1,2-diol to 1,3-dioxane derivatives with phenyltrimethylammonium tribromide in the presence of a catalytic amount of antimony(III) bromide

trans-Stilbene oxide was oxidatively converted to 2-phenyl-1,3-dioxanes with phenyltrimethylammonium tribromide in the presence of various 1,3-diols and a catalytic amount of SbBr3 in DMSO at room temperature. Aromatic 1,2-diol, such as hydrobenzoin, was similarly converted to 2-aryl-1,3-dioxane derivatives under the same reaction conditions.

Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions

Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein-Ponndorf- Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other compounds via Felkin-Ahn control.

A novel mononuclear Fe(III) mono(terpyridine) complex having labile solvent ligands and its catalytic activity

A novel Fe mono(terpyridine) complex was successfully prepared by deliberately choosing the polymer surface-anchored terpyridine as a chelating ligand and it showed an excellent catalytic activity with an easy reusability on the ring-opening reaction of various epoxides by alcohol and water under mild and neutral conditions to give stereospecific and regioselective products.