108475-88-3

Upstream product

• 100-52-7 benzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 94-41-7 benzalacetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 614-47-1 1,3-diphenyl-propen-3-one 

Downstream Products

• 103166-29-6 (2RS,3RS)-2,3-bis-benzoyloxy-1,3-diphenyl-propan-1-one 
• 94002-12-7 1cat_F,3cat_F-diphenyl-propane-1r_F,2c_F,3c_F-triol 
• 102019-10-3 2,3-diacetoxy-1,3-diphenyl-propan-1-one 
• 115229-06-6 3-hydroxy-1,3-diphenyl-propane-1,2-dione-bis-(4-nitro-phenylhydrazone) 
• 103035-93-4 3-hydroxy-1,3-diphenyl-propane-1,2-dione-bis-(2,4-dinitro-phenylhydrazone) 
• 103510-91-4 1r_F,2c_F,3c_F-tris-benzoyloxy-1cat_F,3cat_F-diphenyl-propane 

Relevant academic research and scientific papers

RuCl3/CeCl3/NaIO4: A new bimetallic oxidation system for the mild and efficient dihydroxylation of unreactive olefins

(Chemical Equation Presented) The catalytic dihydroxylation of olefins represents a unique synthetic tool for the generation of two C,O-bonds with defined relative configuration. Whereas OsO4 has been established as a very general dihydroxylati

Cis-dihydroxylation of alkenes with oxone catalyzed by iron complexes of a macrocyclic tetraaza ligand and reaction mechanism by ESI-MS spectrometry and DFT calculations

[FeIII(L-N4Me2)Cl2]+ (1, L-N4Me2 = N,N′-dimethyl-2,11-diaza[3.3](2,6) pyridinophane) is an active catalyst for cis-dihydroxylation of various types of alkenes with oxone at room temperature using limiting amounts of alkene substrates. In the presence of 0.7 or 3.5 mol % of 1, reactions of electron-rich alkenes, including cyclooctene, styrenes, and linear alkenes, with oxone (2 equiv) for 5 min resulted in up to >99% substrate conversion and afforded cis-diol products in up to 67% yield, with cis-diol/epoxide molar ratio of up to 16.8:1. For electron-deficient alkenes including α,β-unsaturated esters and α,β-unsaturated ketones, their reactions with oxone (2 equiv) catalyzed by 1 (3.5 mol %) for 5 min afforded cis-diols in up to 99% yield with up to >99% substrate conversion. A large-scale cis-dihydroxylation of methyl cinnamate (9.7 g) with oxone (1 equiv) afforded the cis-diol product (8.4 g) in 84% yield with 85% substrate conversion. After catalysis, the L-N4Me2 ligand released due to demetalation can be reused to react with newly added Fe(ClO4)2?4H2O to generate an iron catalyst in situ, which could be used to restart the catalytic alkene cis-dihydroxylation. Mechanistic studies by ESI-MS, isotope labeling studies, and DFT calculations on the 1-catalyzed cis-dihydroxylation of dimethyl fumarate with oxone reveal possible involvement of cis-HO-Fe V O and/or cis-O FeV O species in the reaction; the cis-dihydroxylation reactions involving cis-HO-FeV O and cis-O FeV O species both proceed by a concerted but highly asynchronous mechanism, with that involving cis-HO-FeV O being more favorable due to a smaller activation barrier.

The acid accelerated ruthenium-catalysed dihydroxylation. Scope and limitations

Recently, we discovered a significant rate acceleration in RuO 4-catalysed dihydroxylations of olefins by addition of Broensted-acids resulting in a reduction of the catalyst loading to only 0.5 mol%. The present paper gives a full account on the optimisation protocol that led to the discovery of the beneficial influence of protic acids. A strong focus is set on the detailed description of the influence of different reaction parameters on both reactivity and selectivity. In the second part an intense investigation of scope and limitations will be presented. The results provided in this manuscript might lead to a deeper understanding of competing processes that influence the selectivity in RuO4-catalysed dihydroxylations.

Syntheses of zinc complexes with multidentate nitrogen ligands: New catalysts for aldol reactions

The ligands 2,6-bis{[(pyrid-2-ylmethyl)amino]methyl}-pyridine with an N5 pattern and (6-{[(pyrid-2-ylmethyl)amino]methyl}pyrid-2-yl)methanol with an N3O pattern were synthesized. ZnII complexes of the two ligands could be obtained, and the single-crystal X-ray structure of (2,6-bis{[(pyrid-2-ylmethyl)amino]methyl}pyridine)zinc chloride showed Zn coordination to all five nitrogen atoms. The strong complexation of 2,6-bis{[(pyrid-2-ylmethyl)-amino]methyl}pyridine and (6-{[(pyrid-2-ylmethyl)amino]-methyl}pyrid-2-yl)methanol with ZnII were demonstrated by 1H NMR spectroscopic studies and electrospray mass spectrometry. The coupling of 2-hydroxyacetophenone and benzaldehyde was studied in the presence of the prepared Zn complexes, and it was shown that the coupling product was obtained at room temperature in up to 60% yield with 7.5 mol% of the zinc catalyst. The present complexes mimic the active site of the zinc-dependent class II aldolases, where ZnII is coordinated to three nitrogen atoms. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Interactive free energy relationships in the Os(VIII) catalysed oxidation of chalcones by acid bromate: A kinetic study

The kinetics and mechanism of Os(VIII) catalysed oxidation of chalcones by acid bromate with special reference to interactive free energy relationships have been studied. The reaction is zero order in [BrO3-], fractional order in [chalcone] and first order in [Os(VIII)]. The reaction is enhanced by electron releasing substituents both in benzaldehyde and acetophenone moieties. The magnitude of p value obtained for various substituents in benzaidehyde moiety decreased with the introduction of electron releasing groups in acetophenone moiety and vice versa. A linear plot is obtained between ρX(Y) (obtained from the Hammett's plot for various substituents in benzaldehyde moiety) and σY (substituent constant for substituents in acetophenone moiety) with a slope (qY) of 1.02±0.01. Similarly a linear plot is obtained between ρY(X) (obtained from the Hammett's plot for various substituents in acetophenone moiety) and σX (substituent constant for substituents in benzaldehyde moiety) with a slope (qX) of 0.92±0.01. These relationships have been analysed quantitatively in terms of interactive free energy relationships for multiple substituent effects.

Os(VIII) catalysed oxidation of phenyl styryl ketone and substituted phenyl styryl ketones by periodate: Interactive free energy relationship

Kinetics of Os(VIII) catalysed oxidation of phenyl styryl ketone and its substituted analogues by periodate has been investigated in acetic acid + dichloromethane + water medium in the temperature range 298-313 K.The rates are found to be enhanced by electron releasing substituents and retarded by electron withdrawing substituents both in benzaldehyde and acetophenone rings.However, the effect of substituents is more pronounced when they are present in benzaldehyde ring.The magnitude of ρx(y) value obtained from the slope of Hammett's plot for various substituents in benzaldehyde moiety decreases wiht the introduction of electron withdrawing groups in acetophenone moiety and vice versa.A linear plot is obtained between ρx(y) and ?y (substituent constant for substituent in acetophenone moiety) with a slope of 0.36+/-0.01.The plot ρy(x) (obtained from Hammett's plot for various substituents in acetophenone moiety) versus ?x (substituent constant for substituent in benzaldehyde moiety) is also linear with a slope of 0.41+/- 0.01.The results have been analysed in terms of interactive free energy relationship.

Radical Addition to the Carbonyl Carbon Promoted by Aqueous Titanium Trichloride: Stereoselective Synthesis of α,β-Dihydroxy Ketones

Ketyl radicals, formed by chemoselective Ti(III) reduction of α,β-dicarbonyl compounds, add to the carbonyl carbon of aldehydes under mild conditions to afford α,β-dihydroxy ketones in good to excellent yields.Simple diastereoselectivity strongly depends on the bulk of groups bonded to both the ketyl radical and the aldehydic function.The relative configuration of two the keto diols was established by single-crystal X-ray diffractometry.

A STEREOSELECTIVE SYNTHESIS OF α,β-DIHYDROXY KETONES. AN ALDOL REACTION OF ENEDIOL-TYPE CYCLIC VINYLOXYBORANES

α,β-Dihydroxy ketones are synthesized stereoselectively by the aldol reaction of 1,3,2-dioxaboroles, formed from α-hydroxy ketones and phenylboronic acid, and aldehydes.