1603-79-8Relevant articles and documents
Addition of grignard reagents to 1-(N-(Alkoxyoxalyl)-JV-methylamino)-3-methylimidazolium Salts: A general method for α-keto ester synthesis
De Las Heras, Maria A.,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio
, p. 9009 - 9011 (1996)
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Wright
, p. 4883 (1955)
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A trispyrazolylborato iron malonato complex as a functional model for the acetylacetone dioxygenase
Siewert, Inke,Limberg, Christian
, p. 7953 - 7956 (2008)
(Chemical Equation Presented) Position available: A pentacoordinate iron(II) complex that binds and activates dioxygen shows dioxygenase activity and cleaves diethyl phenylmalonate, in analogy to acetylacetone dioxygenase (see scheme). The mechanism for the model compound allows interesting hypotheses to be made about the enzyme function.
Copper-catalysed Oxidation of Hydroxy Compounds by tert-Butyl Hydroperoxide Under Phase-transfer Conditions
Feldberg, Liron,Sasson, Yoel
, p. 1807 - 1808 (1994)
In the presence of quaternary ammonium phase-transfer agents copper salts catalyse the selective oxidative dehydrogenation of alcohols and hydroxy acids by tert-butyl hydroperoxide in aqueous-organic two-phase systems.
VO(OEt)Cl2-induced oxidative deamination
Hirao, Toshikazu,Ohshiro, Yoshiki
, p. 3917 - 3918 (1990)
VO(OEt)Cl2 oxidized 2-phenylglycine derivatives via oxidative deamination and/or decarboxylation giving ethyl benzoate and ethyl phenylglyoxylate.
Metal-free oxidative esterification of acetophenones with alcohols: A facile one-pot approach to α-ketoesters
Guo, Shiyu,Dai, Zhongxue,Yang, Zhao,Zhu, Ning,Wan, Li,Li, Xin,Liu, Chengkou,Fang, Zheng,Guo, Kai
, p. 98422 - 98426 (2016)
A novel and efficient oxidative esterification method for the synthesis of α-ketoesters has been developed under mild and environmentally benign conditions, which is a facile one-pot approach to α-ketoesters from commercially available acetophenones with alcohols, especially under metal-free conditions, with broad substrate scope. A possible mechanism is proposed on the basis of a series of control experiments and DMSO18 isotopic labelling experiments.
A remarkable effect of quaternary ammonium bromide for the N- hydroxyphthalimide-catalyzed aerobic oxidation of hydrocarbons
Matsunaka, Katsuhisa,Iwahama, Takahiro,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 2165 - 2168 (1999)
A methodology for the aerobic oxidation of organic substrates in the absence of any metal catalyst has been established using combined catalytic system consisting of N-hydroxyphthalimide and quaternary ammonium bromide. Thus, various hydrocarbons were successfully oxidized under dioxygen atmosphere to the corresponding oxygenated compounds in good selectivities.
FACTORS AFFECTING DYE SENSITISED PHOTO-OXIDATION REACTIONS; THE EFFECT OF OXYGEN CONCENTRATION AND ITS USE TO PROBE THE MECHANISM OF DECARBOXYLATION OF α-OXO-CARBOXYLIC ACIDS AND ESTERS
Davidson, R. Stephen,Goodwin, Dean,Pratt, Julie E.
, p. 2373 - 2380 (1983)
The dye sensitised photo-oxidation of α-oxo-carboxylic acids and esters leads to the production of carbon dioxide.The yield of carbon dioxide is dependent upon the oxygen concentration.This, together with the fact that carbon dioxide evolution can be observed in the absence of oxygen, is in accord with the view that the decarboxylation reactions involve an initial dye-substrate interaction rather than a singlet oxygen mediated reaction.
Unraveling two pathways for NHPI-mediated electrocatalytic oxidation reaction
Xu, Leitao,Yi, Yangjie,Hu, Sideng,Ye, Jiao,Hu, Aixi
, (2021/11/30)
Two pathways for N-hydroxyphthalimide (NHPI)-mediated electrocatalytic oxidation using phenylacetate derivatives as template substrates were first reported for benzylic C[sbnd]H oxidation to oxygenated and non-oxygenated products. DFT calculation indicates that the hydrogen-atom transfer (HAT) process between phthalimido-N-oxyl (PINO) and substrate is a rate-determined step. Aromatic α-keto esters and 2-((1,3-dioxoisoindolin-2-yl)oxy)-2-aryl acetate obtained by cross-coupling between benzylic radical and PINO can be selectively synthesized through controlling the concentration of PINO radical. This method provides a deep understanding for selective weak C[sbnd]H oxidation using NHPI as redox mediator.
Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters
Chu, Changhu,Dong, Wenwen,Lin, Jia,Teng, Jiangge,Wang, Zhiwei,Zhao, Rong
, p. 6120 - 6126 (2021/07/21)
By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.
Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes
Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil
, p. 6709 - 6713 (2021/09/08)
A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.