2314-78-5Relevant academic research and scientific papers
The oxidation of the alpha-carbon of amines in hydrothermal condition: An alternative synthetic route of compounds containing amide bond
Bai, Xueyin,Liu, Ziwei,Ye, Kaiqi,Wang, Yu,Zhang, Xianlong,Yue, Huijuan,Tian, Ge,Feng, Shouhua
, p. 319 - 321 (2014)
Here we report experimental evidence for the simple synthesis of N,N-diethylhydroxylamine and an amide bond formation reaction from oxidation of the alpha-carbon of tertiary amines by the reaction of triethylamine and hydrogen peroxide in hydrothermal conditions. It is proved that 120 C is a turning point: when the temperature is lower than that, the main product is N,N-diethylhydroxylamine as a result of a cope rearrangement reaction mechanism; on the contrary, the product is more complex and the main products are amides via a radical chain mechanism involving three steps: initiation, propagation, and oxidation, followed by decarbonylation and electrocyclization because the radical is easier to form under high temperature.
Valuable new platform chemicals obtained by valorisation of a model succinic acid and bio-succinic acid with an ionic liquid and high-pressure carbon dioxide
Silva, Daniel,Bogel-Lukasik, Ewa
, p. 4048 - 4060 (2017/09/07)
The potential application of biomass and catalysts is crucial to form a bridge between the emerging bio-based industry and the current process technology. Using this approach to succinic acid, a biomass derived acid, might lead to new routes for derivative production, opening its transition to the industrial scale. A considerable number of succinic acid-based products were obtained in this work in advanced, one-pot processes executed in a green solvent, supercritical carbon dioxide. Ionic liquids, which present an alternative to volatile and flammable solvents, allowed for a subsequent transformation of carbohydrate rich renewable feedstock by a simple reaction in alternative media. Reactions give a possibility of conversion of a cheap lignocellulosic biomass to succinic acid-based products, such as ethanol having a potential application in biorefinery, as well as to pyrrolidine-2,5-diones, representing antibiotics and to succinic acid esters, valuable platform chemicals. Mechanistic analysis of the formation of reaction products was successfully developed. The valorisation of a model succinic acid was compared with the valorisation of a bioderived succinic acid under identical reaction conditions and the results are discussed. The palladium catalyst nanoparticles formed seem to be stabilised by ionic liquids allowing for five successive cycles with efficient conversion and selectivity in the hydrogenation of bio-succinic acid. The presented valorisation of a biomass derived carboxylic acid is an excellent starting point for derivative production.
Anodic Oxidation of Amides and Lactams Using N-Hydroxyphthalimide as a Mediator
Masui, Masaichiro,Hara, Seijiro,Ozaki, Shigeko
, p. 975 - 979 (2007/10/02)
Indirect electrochemical oxidation of amides and N-alkyllactams was performed using N-hydroxyphthalimide as a mediator.A carbonyl group was introduced in good yield at the α-carbon to the nitrogen of the compounds.Keywords - anodic oxidation; mediator; amide; N-alkyllactam; N-hydroxyphthalimide; imide; N-acyllactam; glassy-carbon electrode
