87482-83-5

Upstream product

• 996-82-7 sodium diethylmalonate 
• 79449-94-8 (chloromethyl-d)benzene 
• 5292-53-5 diethyl benzalmalonate 
• 3481-15-0 benzyl alcohol-d1 
• 100-52-7 benzaldehyde 

Downstream Products

• 87482-85-7 benzyl-α-d-malonic acid 

Relevant academic research and scientific papers

Tuning the lewis acidity of boranes in frustrated lewis pair chemistry: Implications for the hydrogenation of electron-poor alkenes

An analysis of the metal-free reduction of electron deficient olefins by frustrated Lewis pairs indicates that the rate-determining step might be either the heterolytic cleavage of H2 to form an -onium borohydride salt, or the subsequent transfer of the hydride moiety to the substrate following a Michael-type addition reaction. While the use of strong Lewis acids such as B(C6F5)3 facilitates the first of these processes, hydride transfer to the olefin should be contrarily favoured by the use of weak Lewis acids which, for this very same reason, might be unable to promote the prior H2 split. After systematic testing of several boranes of different Lewis acidity (assessed by using the Childs' method) and steric demand, an optimal situation that employs tris(2,4,6-trifluorophenyl) borane was reached. Mixtures of this borane with 1,4-diazabicyclo[2.2.2]octane (DABCO) exhibited excellent catalytic activity for the hydrogenation of alkylidene malonates. In fact, this transformation could be achieved under milder conditions than those we reported previously. Moreover, the reaction scope could be expanded to other electron deficient olefins containing esters, sulfones or nitro functionalities as electron-withdrawing substituents.

Metal-free hydrogenation of electron-poor allenes and alkenes

The poorer, the better: A metal-free catalytic procedure for the reduction of electron-poor allenes and alkenes has been developed. The method employs a frustrated Lewis pair based catalyst. 1,4-Diazabicyclo[2.2.2]octane (DABCO)/B(C6F5)3 was shown to be the best combination in optimization studies. Copyright

HYDRIDE TRANSFER IN THE REDUCTION OF SUBSTITUTED BENZYLIDENE MALONIC DIESTERS BY COENZYME NAD(P)H MODEL

The reduction of substituted benzylidene malonic diesters by 1-benzyl-1,4-dihydronicotinamide (BNAH) is catalyzed by magnesium perchlorate.Kinetic isotope effects studies show that the C(4)-H bond cleavage in BNAH is involved in the rate determining step.Spectroscopic investigations have revealed that the ternary complex is formed in the ground state while complexation of substrate with magnesium ion is rate enhancing.

Bromide Ion Promoted β-Elimination in α-Bromo Ester Substrates. Evidence for an Intermediate in the E2C Reaction

The TDKIE criteria of transition state geometry in H-transfer reactions have been applied in the title reactions; a bent transition state consistent with the geometry of the E2C reaction has been verified by the results of intramolecular and intermolecular competition modes of determining kH/kD as a function of temperature.The extraordinary magnitude measured for the α secondary deuterium isotope effect in the E2C mechanism is reconciled with a very loose transition state and an acute angle of H-abstraction in the course of rearward approach to Cα by the promoter base.The virtual identity of the inter- and intramolecular isotope effects can be correlated by the assumption of a reaction intermediate of trigonal-bipyramid structure surrounding Cα and in which the abstractable H and D atoms are equally available to the action of the promoter base.The properties of this intermediate (4), by way of contrast with the transition state of an SN2 process, are discussed in detail.