75406-29-0Relevant academic research and scientific papers
Synthesis of arylacetates from benzylic alcohols and oxalate esters through decarboxylative coupling
Gruenberg, Matthias F.,Goossen, Lukas J.
supporting information, p. 7334 - 7337 (2013/06/27)
Follow that dream: By combining a reversible transesterification between benzylic alcohols and dialkyl oxalates with catalytic decarboxylation of the resulting esters, a regiospecific C-C-bond-forming reaction to give α-arylacetates was achieved. In the overall process, CO2 and a volatile alcohol are the only byproducts. Various α-arylacetates were thus synthesized in high yields from easily accessible starting materials in the presence of catalytic amounts of Pd(OAc)2, dppp, and DABCO (see scheme). Copyright
Environmentally friendly transesterification and transacylation reactions under libr catalysis
Abaee, M. Saeed,Akbarzadeh, Elahe,Sharifi, Roholah,Mojtahedi, Mohammad M.
experimental part, p. 757 - 761 (2011/07/08)
A room-temperature, convenient transesterification of various esters, induced by catalytic amounts of lithium bromide and diethylamine in a solvent-free environment, is described. Products are obtained in good purity by simple filtration to remove the catalyst and evaporation of the volatile portion. The procedure has also been successfully applied to transacetylation and aminolysis of esters. Springer-Verlag 2010.
Electro-organic reactions. Part 27. The mechanism of cathodic cleavage of activated esters; oxalates, squarates and oxamates
Islam, Nazar-ul,Sopher, David W.,Utley, James H.P.
, p. 959 - 970 (2007/10/02)
Esters of oxalic acid, 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid), and oxamic acid, are reduced cathodically at modest potentials. In aprotic solvent, and on the cyclic voltammetric time scale, the esters are cleaved to the corresponding alkane. For oxalates, the mechanism of cathodic cleavage was investigated thoroughly by voltammetry, coulometry, and detailed product analysis. On the time scale of controlled potential electrolysis the rapid electrogenerated base-catalysed hydrolysis of the esters by adventitious water competes with cathodic cleavage. Similarly, rapid base-catalysed transesterification involving oxalates and added alcohols is observed which provides a practical method of reductively cleaving alcohols to alkanes by co-electrolysis of a mixture of alcohol and readily available oxalate (e.g. diethyloxalate). The leaving group in such cathodic fragmentation is the half-ester anion and the efficiency of reaction depends on the stability of the other, radical, fragment.
ELECTRO-ORGANIC REACTION: PART 28. PREPARATIVE APPLICATIONS OF THE OXALATE CATHODIC CLEAVAGE REACTION INCLUDING ONE-POT CONVERSIONS OF ALDEHYDES AND KETONES
Nazar-ul-Islam,Sopher, David W.,Utley, James H. P.
, p. 2741 - 2748 (2007/10/02)
Alcohols and vicinal diols, when co-electrolysed with oxalate esters, undergo transesterification catalysed by cathodically generated base.Under mild conditions at modest cathodic potentials the esters formed in situ give good yields of the corresponding alkanes and alkenes.Furthermore, because diols (pinacols) and alcohols may be efficiently prepared electrochemically from aldehydes and ketones, a one-pot conversion of the carbonyl compounds into alkanes and alkenes has been devised.The method involves prior electrolysis to alcohol or pinacol, addition of an oxalate ester, and further electrolysis for reductive de-oxygenation.Good results are obtained for aromatic ketones and aldehydes.Several oxalate esters have been used in such reactions; diethyloxalate is the most convenient.Esters of squaric acid and of oxamic acid undergo cathodic de-oxygenation but are not convenient in preparative use.
