130028-18-1Relevant articles and documents
p-Cymene as Solvent for Olefin Metathesis: Matching Efficiency and Sustainability
Granato, Artur V.,Santos, Alexandra G.,dos Santos, Eduardo N.
, p. 1832 - 1837 (2017)
The underexploited biorenewable p-cymene is employed as a solvent for the metathesis of various substrates. p-Cymene is a nontoxic compound that can be obtained in large amounts as a side product of the cellulose and citrus industry. For the cross-metathesis of estragole with methyl acrylate, this solvent prevents the consecutive double-bond isomerization of the product and affords the best yield of all solvents tested. Undesired consecutive isomerization is a major challenge for many substrates in olefin metathesis, including pharmaceutical precursors, and the use of p-cymene as a solvent may be a way to prevent it. This solvent results in a better metathesis performance than toluene for the three substrates tested in this work, matching its performance for two other substrates.
Operationally simple and highly (E)-styrenyl-selective heck reactions of electronically nonbiased olefins
Werner, Erik W.,Sigman, Matthew S.
supporting information; experimental part, p. 9692 - 9695 (2011/08/06)
Simple, mild, and efficient conditions are reported for a Pd 0-catalyzed Heck reaction that delivers high yields and selectivity for (E)-styrenyl products using electronically nonbiased olefin substrates bearing a range of useful functionality. Preliminary mechanistic studies demonstrate that the σ-donating DMA solvent is crucial for high selectivity. Further studies suggest that the catalyst distinguishes between β-hydrogens on the basis of their relative hydridic character, in contrast to previously reported PdII-catalyzed oxidative reaction conditions.
Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates
Davies, Huw M.L.,Yang, Jaemoon,Manning, James R.
, p. 665 - 673 (2007/10/03)
An improved one-flask synthesis of various methyl 2-diazo-4-aryl and 4-heteroaryl-3-butenoates, precursors to donor/acceptor substituted carbenoids, is described. Their Rh2(S-DOSP)4 catalyzed reaction with 1-acetoxy-3,4-dihydronaphth
A FACILE ONE-STEP SYNTHESIS OF β,γ-UNSATURATED CABOXYLIC ACID ESTERS VIA 1,2-CARBONYL TRANSPOSITIONS OF α,β-UNSATURATED KETONES
Mathew, Felix,Myrboh, B.
, p. 3757 - 3758 (2007/10/02)
Reaction of α,β-unsaturated ketone, 1, with lead(IV)acetate and borontrifluoride etherate in the presence of methanol yielded the β,γ-unsaturated esters, 2, in a single step procedure, at room temperature.
