36239-19-7

Upstream product

• 134-81-6 benzil 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 5284-44-6 trans-1,2-dideuteriostilbene 
• 15951-99-2 1,2-dichloro-1,2-diphenylethane 

Downstream Products

• 3592-47-0 Benzaldehyde-d 
• 34243-41-9 (α-deuterio-benzaldehyde)diethylacetal 
• 75337-24-5 2-Deutero-2-phenyl-1,3-dioxolan 
• 25333-24-8 3-benzoylpropionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen-Deuterium Exchange Reactions

Herein we have developed a reversible hydrogen-deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of compatibility of functional groups was achieved.

A Revised Mechanism for the Kinugasa Reaction

Detailed kinetic analysis for the Cu(I)-catalyzed Kinugasa reaction forming β-lactams has revealed an anomalous overall zero-order reaction profile, due to opposing positive and negative orders in nitrone and alkyne, respectively. Furthermore, the reaction displays a second-order dependence on the catalyst, confirming the critical involvement of a postulated bis-Cu complex. Finally, reaction progress analysis of multiple byproducts has allowed a new mechanism, involving a common ketene intermediate to be delineated. Our results demonstrate that β-lactam synthesis through the Kinugasa reaction proceeds via a cascade involving (3 + 2) cycloaddition, (3 + 2) cycloreversion, and finally (2 + 2) cycloaddition. Our new mechanistic understanding has resulted in optimized reaction conditions to dramatically improve the yield of the target β-lactams and provides the first consistent mechanistic model to account for the formation of all common byproducts of the Kinugasa reaction.

Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.

Oxidative behaviours and relative reactivities of some aliphatic, heterocyclic and aromatic aldehydes towards bis(dihydrogentellurato)cuprate(III) and argentate(III) in alkaline medium

The oxidative behaviours and relative reactivities of some aliphatic aldehydes, XCHO (where X = H-, Me-, MeCH2-, Me2CH-), 2-furaldehyde and aromatic aldehydes, YC6H4CHO (where Y = -H, - NO2, - Cl and - OMe) towards bis(dihydrogentellurato)metallate(III) ion (where MIII = CuIII or AgIII) in alkaline medium have been investigated. The reactions are first order each in [aldehyde] and [MIII(H2 TeO6)2]5- but the rate is independent of [OH-]. The values of kobs in the oxidation of some aliphatic aldehydes, 2-furaldehyde and benzaldehyde in aqueous medium follow the order: Me2CH - > MeCH2 - > Me - > H - > C4H3O - > C6H5 -. The electron withdrawing substituents facilitate the rate of oxidation of benzaldehyde whereas electron donating substituents have opposite effect and the values of kobs follow the order: - NO2> H > - Cl > - OMe. The pseudofirst order rate constants decrease considerably in benzaldehyde-d1, than benzaldehyde under comparable condition of experiments. Irrespective of whether the substrate is aliphatic or aromatic, the oxidation reactions occur via free radical mechanism although the substituent and isotope effects in the oxidations of aromatic aldehydes indicate that C - H bond cleavage via proton transfer may also occur. The activation parameters of the reactions have been determined and the mechanism of the reactions is discussed.

Synthesis of Z- and E-[2,3-2H2] and [2,3-3H2]-1,1-dichloro-2,3-diphenylcyclopropane (2H- and 3H-analog II and its trans isomer)

2H and 3H labelled Z- and E-1,1-dichloro-2,3-diphenylcyclopropane (1 and 2) were synthesized starting from NaB2H4 and NaB3H4 reduction of benzil. The resulting glycols were transformed to t

Kinetics and Mechanism of the Oxidation of Aromatic Aldehydes by Hexachloroiridate(IV)

The kinetics of oxidation of benzaldehyde and some substituted benzaldehydes by hexachloroiridate(IV) have been studied spectrophotometrically in the visible region.The reaction is first order in benzaldehyde and in iridium(IV).The influence of acidity on the reaction is small.The activation parameters of the reaction have been calculated.The oxidation reaction is found to have a deuterium isotope effect, kH/kD, of 7.0, indicating that the cleavage of the C-H bond of the aldehyde is the rate-determining step.The reaction appears to be of outer-sphere type and occurs through the intermediate formation of free radicals.