591-63-9Relevant academic research and scientific papers
Acrylates via Metathesis of Crotonates
Schweitzer, Dirk,Snell, Kristi D.
supporting information, p. 715 - 720 (2015/07/27)
Crotonic acid has the potential to be produced from renewable resources at low cost but currently has a limited market. We are investigating catalytic routes to exploit the functionalities of crotonic acid to produce a range of established industrial chemicals. Here we report our work on converting crotonates to acrylates, where a cost-competitive bio-based alternative can provide a market advantage. Our optimized reaction conditions for the cross-metathesis between crotonates and ethylene resulted in an increase in catalyst turnover numbers by 2 orders of magnitude compared with literature values. Control experiments showed the cross-metathesis with ethylene to be an equilibrium reaction. The turnover-number-limiting factor was found to be the stability of the metathesis catalyst.
Efficient, stable, and reusable Lewis acid-surfactant-combined catalyst: One-pot Biginelli and solvent-free esterification reactions
Qiu, Yunfeng,Sun, Hongnan,Ma, Zhuo,Xia, Wujiong
, p. 76 - 82 (2014/06/10)
Cerium(III) trislaurylsulfonate (Ce(LS)3), a Lewis acid and surfactant combined catalyst, was prepared and characterized by SEM, SEM-EDX, XRD, NMR, FT-IR, TG, and elemental analysis. Ce(LS)3 was found to be stable and efficient to catalyze one-pot Biginelli and solvent-free esterification reactions. Furthermore, Ce(LS)3 is easy to recycle after reaction by pouring into cold water and filtration. Present work will shed deep insight into the understanding of the catalytic nature of LASCs, and extend its application in important organic transformations.
One-pot ester synthesis from allyl and benzyl halides and alcohols by palladium-catalyzed carbonylation
Tommasi, Sara,Perrone, Serena,Rosato, Francesca,Salomone, Antonio,Troisi, Luiginio
experimental part, p. 423 - 430 (2012/03/11)
A mild and efficient one-pot synthesis of esters based on the Pd-catalyzed alkoxy- and aryloxycarbonylation of allylic and benzylic halides is described. The methodology has been applied to primary, secondary, and tertiary alcohols as well as to phenol derivatives. The O-protection of some biologically relevant molecules is also reported. Georg Thieme Verlag Stuttgart New York.
Catalytic amide-mediated methyl transfer from silanes to alkenes in Fujiwara-Moritani oxidative coupling
Rauf, Waqar,Brown, John M.
scheme or table, p. 4228 - 4230 (2009/03/12)
(Chemical Equation Presented) Intramolecular assistance: Carbon-bound trimethylsilyl groups are activated intramolecularly by a carbonyl group and can participate in Heck reactions under oxidative conditions. Good stereoselectivities are obtained for a range of di-and trisubstituted alkenes (see example).
Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism
Iqbal,Srivastava
, p. 3155 - 3170 (2007/10/02)
Cobalt(II) chloride in acetonitrile catalyses the cleavage of a wide variety of ethers with acyl halides under mild conditions to give the corresponding esters in good yields. Acyclic aliphatic ethers are cleaved to the corresponding ester and chlorides whereas the cyclic aliphatic ethers give rise to the ω-chloroesters. The benzyl ethers can be converted to the corresponding esters along with the formation of benzyl chloride and benzyl acetamide. A comparative study for the cleavage of allyl and benzyl ether has revealed that benzyl ether can be selectively cleaved in presence of the allyl ethers. The oxiranes can be cleaved in highly regioselective manner to the corresponding-β-chloroesters. The vinyl ethers undergo sp2-hybridised carbon-oxygen bond cleavage under these conditions. Based on product analysis, a mechanism involving electron transfer followed by O-acylation and S(N)1 or S(N)2 attack by chloride-ion is discussed.
Electrocatalytic Oxidation of Allylic Ethers, Dihydropyran and Phenol Using a Polypyridyl Complex of Ruthenium(IV)
Campos, Jose Luiz,Giovani, Wagner F. De,Romero, Jose Ricardo
, p. 597 - 599 (2007/10/02)
An electrocatalytic procedure is described for the oxidation of allyl butyl ether, (E/Z)-2-butenyl butyl ether, dihydropyran and phenol using the ruthenium(IV) oxidant 2+.The resulting products were respectively, butyl acrylate (42percent), butyl (E/Z)-2-butenoate (53percent), 2,3-dihydro-4-pyranone (40percent) and o-benzoquinone (71percent).
