1126-76-7

Upstream product

• 93-59-4 Perbenzoic acid 
• 768-56-9 4-Phenylbut-1-ene 
• 39972-78-6 allyl t-butyl peroxide 
• 141036-65-9 4-Phenyl-1-p-tolylsulfanyl-butan-2-ol 
• 89368-01-4 2-styryloxirane 
• 104-53-0 3-phenyl-propionaldehyde 
• 6814-64-8 methylenedimethyl sulfurane 
• 141916-52-1 4-phenyl-1-chloro-2-butanol 
• 569363-96-8 methyloctylsulfonioacetate 
• 6921-34-2 benzylmagnesium chloride 
• 1589-82-8 phenylmagnesium bromide 
• 96937-97-2 4-Phenyl-1-((R)-toluene-4-sulfinyl)-butan-2-one 
• 55941-47-4 4-Phenyl-1-((R)-toluene-4-sulfinyl)-butan-2-ol 
• 2181-42-2 trimethylsulphonium iodide 

Downstream Products

• 2550-26-7 4-Phenyl-2-butanone 
• 91553-20-7 dimethyl-(β-oxy-δ-phenyl-butyl)-amine 
• 1992-49-0 1-phenyl-3-octanol 
• 119405-89-9 (Z)-oct-3-en-1-ylbenzene 
• 119405-88-8 ((E)-Oct-3-enyl)-benzene 
• 115045-60-8 1-(3-butyl-3-butenyl)benzene 
• 79407-23-1 2-Hydroxy-5-[2-(2-hydroxy-4-phenyl-butylamino)-ethoxy]-benzamide 
• 65674-08-0 4-phenyl-1,2-epithiobutane 
• 18328-11-5 3-benzyl propionaldehyde 
• 58040-28-1 1-Benzylamino-4-phenyl-butan-2-ol 
• 2344-70-9 1-phenyl-3-butanol 
• 3360-41-6 4-phenyl-butan-1-ol 
• 117974-11-5 (D,L)-4-phenyl-2-hydroxy-1-butylamine 

Relevant academic research and scientific papers

Microwave-assisted copper-catalyzed stereoselective ring expansion of three-membered heterocycles with α-diazo-β-dicarbonyl compounds

Microwave-assisted copper-catalyzed ring expansions of three-membered heterocycles with α-diazo-β-dicarbonyl compounds were investigated. Thiiranes generated 3-acyl-5,6-dihydro-1,4-oxathiines in the presence of copper sulfate and trans-3-acyl-5,6-dihydro-1,4-oxathiines as stereospecific products for 1,2-disubstituted cis-thiiranes through an intramolecular SN2 process. Oxiranes gave rise to 2-acyl-5,6-dihydro-1,4-dioxines under the catalysis of copper hexafluoroacetylacetonate and cis-3-acyl-5,6-dihydro-1,4-dioxines as stereospecific products for 1,2-disubstituted cis-oxiranes via an intimate ion-pair mechanism. The current method provides a direct and simple strategy in efficient preparation of 3-acyl-5,6-dihydro-1,4-oxathiines and 2-acyl-5,6-dihydro-1,4-dioxines, important agents in medicinal and agricultural chemistry, from readily available thiiranes and oxiranes, respectively.

Dioxidomolybdenum(VI) complexes containing ligands with the bipyrrolidine backbone as efficient catalysts for olefin epoxidation

Air-stable chiral dioxidomolybdenum(VI) complexes of the type [MoO 2(L)] (L = L12-; 1, L = L22-, 2) were prepared by the reaction of [MoO2Cl2] with the bis(phenol) ligands 1,4-bis(2-hydroxy-benzyl)-(S,S)-2,2′-bipyrrolidine [(S,S)-H2L1] and 1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-(S,S)-2,2′-bipyrrolidine [(S,S)-H2L2). They were characterized by NMR spectroscopy, mass spectrometry, elemental analysis, and single-crystal X-ray diffraction analysis, which revealed a distorted octahedral coordination geometry around the molybdenum(VI) center with a cis-α configuration. The Mo-Ooxo bond lengths are almost equal and vary only between 1.701 and 1.7091 A. Complexes 1 and 2 were found to be efficient and selective catalysts for various olefin epoxidation reactions. Catalyst loadings of 0.5 mol-%, the use of 2 equiv. of oxidant (tert-butyl hydroperoxide), as well as unchanged catalyst performance over three consecutive catalytic runs demonstrate the excellent stability of the catalysts. Various challenging substrates including 1-octene or limonene were converted selectively to their corresponding epoxides. However, no asymmetric induction was observed. The cis-α isomers of dioxidomolybdenum complexes with a chiral backbone exhibit higher catalytic epoxidation activity than the related cis-β complexes. Copyright

Metal-free epoxidation of alkenes with molecular oxygen and benzaldehyde under visible light irradiation

A new convenient metal-free oxidation protocol of a wide variety of alkenes with molecular oxygen and benzaldehyde under visible light irradiation of fluorescent lamp afforded their corresponding epoxides in 49-99% yields. Georg Thieme Verlag Stuttgart.

Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes

(Matrix presented) A novel protocol for the generation of sulfur ylides is described. The overall process involves thermal decarboxylation of a carboxymethyl-sulfonium betaine to give a sulfur ylide that, in the presence of an aldehyde, affords the corresponding terminal oxirane. Yields were found to correlate with the electron deficiency of the aryl aldehyde. In situ generation of betaine in the presence of an aldehyde successfully afforded the desired oxirane in moderate yield, thus demonstrating the feasibility of a catalytic process.

New molybdenum catalysts for alkyl olefin epoxidation. Their implications for the mechanism of oxygen atom transfer

We report here the design, synthesis, and characterization of new (dioxo)Mo(VI) epoxidation catalysts based on monoanionic tridentate ligands. Two important features distinguish these catalysts from those previously reported. First, their coordination env

Chemoselective Hydrogenation of the Double Bond of Vinyl Epoxides with Homogeneous Palladium and Iridium Catalysts

The selective hydrogenation of the double bond of vinyl epoxides is catalyzed by either the species generated by treatment of the binuclear palladium complex, t2PH)PdPBut2>2 with oxygen, or by the cationic iridium(I) complex, BF4, to produce the corresponding saturated epoxides at room temperature, and with good selectivity.

2-Azaadamantane N-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities

The chemoselective oxidation of alcohols containing electron-rich sulfur functionalities (e.g., 1,3-dithianes and sulfides) into their corresponding carbonyl compounds with the sulfur groups can sometimes be a demanding task in modern organic chemistry. A reliable method for this transformation, which features azaadamantane-type nitroxyl radical/copper catalysis using ambient air as the terminal oxidant is reported. The superiority of the developed method was demonstrated by comparing it with various conventional alcohol oxidation methods.

Dioxomolybdenum(VI) complexes with pyrazole based aryloxide ligands: Synthesis, characterization and application in epoxidation of olefins

Synthesis, characterization, and epoxidation chemistry of four new dioxomolybdenum(VI) complexes [MoO2(L)2] (1-4) with aryloxide-pyrazole ligands L = L1-L4 is described. Catalysts 1-4 are air and moisture stable and easy to synthesize in only three steps in good yields. All four complexes are coordinated by the two bidentate ligands in an asymmetric fashion with one phenoxide and one pyrazole being trans to oxo atoms, respectively. This is in contrast to the structure found for the related aryloxide-oxazoline coordinated Mo(VI) dioxo complex 5. This was confirmed by the determination of the molecular structures of complexes 1-3 by X-ray diffraction analyses. Compounds 1-4 show high catalytic activities in the epoxidation of various olefins. Cyclooctene (S1) is converted to its epoxide with high activity, whereas the epoxidation of styrene (S2) is unselective. Internal olefins (S3 and S4) are also acceptable substrates, as well as the very challenging olefin 1-octene (S5). Catalyst loading can be reduced to 0.02 mol % and the catalyst can be recycled up to ten times without significant loss of activity. Supportive DFT calculations have been carried out in order to obtain deeper insights into the electronic situation around the Mo atom.

A General Diastereoselective Strategy for Both cis- and trans-2,6-Disubstituted Tetrahydropyrans: Formal Total Synthesis of (+)-Muconin

A protocol for general diastereoselective tandem dihydroxylation followed by SN2 cyclization was developed for the convenient and efficient synthesis of cis- and trans-2,6-disubstituted tetrahydropyrans from ζ-mesyloxy α,β-unsaturated esters. T

Aryl-substituted sulfonium betaines: Preparation and use in the epoxidation of aldehydes

Thermally induced decarboxylation of carboxymethylsulfonium betaines results in formation of the corresponding sulfur ylides in situ. Decarboxylation rates for a range of arylcarboxymethylsulfonium betaine salts have been determined using NMR spectroscopy, and the efficiency of ylide generation and trapping has been evaluated via methylidene transfer to a range of aldehydes to form epoxides.