15206-55-0Relevant articles and documents
Rhodium catalysed synthesis of seleno-ketals: Via carbene transfer reactions of diazoesters
Jana, Sripati,Aseeva, Polina,Koenigs, Rene M.
, p. 12825 - 12828 (2019)
Herein, we report on rhodium catalysed carbene transfer reactions of diazoesters with diselenides that result in the formal insertion reaction of the carbene fragment into the Se-Se bond to give seleno-ketals in up to 96% yield (35 examples) via an ionic mechanism.
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Ohno et al.
, p. 21,26 (1977)
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HALIDE-DIRECTED NITRILE HYDROLYSYS
Photis, James M.
, p. 3539 - 3540 (1980)
Sodium bromide is an effective catalyst for promoting the hydrolysis of aroyl cyanides such that loss of the cyano group is greatly minimized.
Oxidations of Dihydroxyalkanoates to Vicinal Tricarbonyl Compounds with a 4-BzoTEMPO-Sodium Bromite System or by Indirect Electrolysis Using 4-BzoTEMPO and Bromide Ion
Inokuchi, Tsutomu,Liu, Ping,Torii, Sigeru
, p. 1411 - 1414 (1994)
An efficient access to vicinal dioxoalkanoates, one of structural elements of potent competitive inhibitors of hydrolytic enzyme, from 2,3-dihydroxyalkanoates has been developed, which features an one-step procedure with a mild oxidizing system using recyclable 2, 2, 6, 6-tetramethylpiperidine-1-oxyl in combination with NaBrO2*3H2O or electrogenerated active bromine species as a real oxidant.
A novel method for synthesis of α-keto esters with phenyliodine(III) diacetate
Xie, Yuanyuan,Liu, Jiwei,Huang, Yingyi,Yao, Lixia
, p. 3793 - 3795 (2015)
A rapid and efficient synthesis of α-keto esters from β-ketonitriles using phenyliodine(III) diacetate is reported. This protocol gave α-keto esters in good yields. This is the first time to report the application of hypervalent iodine(III) reagents in the synthesis of α-keto esters. A plausible reaction mechanism is proposed.
An efficient method for synthesis of α-keto acid esters from terminal alkynes
Li, Lian-Sheng,Wu, Yu-Lin
, p. 2427 - 2430 (2002)
α-Keto acid esters can be easily prepared in high yields in two steps from terminal alkynes via bromination and oxidation. This strategy provides a versatile access to the synthesis of biologically important natural products with an α-keto acid moiety.
5,10,15,20-Tetraphenylporphyrinatorhodium(III) iodide catalyzed cyclopropanation reactions of alkenes using glycine ester hydrochloride
Barrett, Anthony G. M.,Braddock, D. Christopher,Lenoir, Isabelle,Tone, Hitoshi
, p. 8260 - 8263 (2001)
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Reactivity of methyl mandelate-Ti(IV)-enediolate: Oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation
Clerici, Angelo,Pastori, Nadia,Porta, Ombretta
, p. 4174 - 4176 (2005)
Methyl mandelate undergoes quantitative oxidative homocoupling on treatment with TiCl4/amine at room temperature. In the presence of ArCHO, quantitative syn-diastereo-selective aldol condensation takes over the dimerization, whereas exclusive M
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Baer,Kates
, p. 1482 (1945)
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Amine degradation by 4,5-epoxy-2-decenal in model systems
Zamora, Rosario,Gallardo, Emerenciana,Hidalgo, Francisco J.
, p. 2398 - 2404 (2006)
The reactions of 4,5-epoxy-2-decenal with octylamine, benzylamine, and 2-phenylglycine methyl ester were studied to investigate if amines may suffer a Strecker type degradation by epoxyalkenals analogously to amino acids. In addition to other reactions, the studied amines were converted into their corresponding Strecker aldehydes (octanal, benzaldehyde, and methyl 2-oxo-2-phenylacetate, respectively) to an extent that depended on the pH, the temperature, the amount of epoxyalkenal, and the amine involved. Each amine exhibited an optimum pH for the reaction, but the corresponding Strecker aldehydes were produced to a significant extent within a broad pH range. In addition, the temperature mostly influenced the reaction rate, which was increased between 6.5 and 9.5 times when the reaction was carried out at 60°C than when it took place at 37°C. Furthermore, Strecker aldehyde formation was linearly correlated with the amount of the epoxyalkenal present in the reaction mixture. Nevertheless, the reaction yield mostly depended on the amine involved. Thus, octylamine only produced trace amounts of octanal, benzylamine was converted into benzaldehyde with a yield of 4.3%, and 2-phenylglycine methyl ester was converted into methyl 2-oxo-2-phenylacetate with a reaction yield of 49%. All of these results suggest that suitable amines can be degraded by epoxyalkenals to their corresponding Strecker aldehydes to a significant extent.
Mechanistic Investigation of the Oxidation of the Carbanion of Methyl 2-Methoxy-2-phenylacetate by an Isoalloxazine
Novak, Michael,Bruice, Thomas C.
, p. 372 - 374 (1980)
Evidence from product studies and radical trapping experiments indicates that the mechanism of the oxidation of the carbanion of methyl 2-methoxy-2-phenylacetate by a model flavin compound in basic methanol is free radical in nature.
Benzylic and allylic oxidations with bis(trifluoroacetoxyiodo)benzene and tert -butyl hydroperoxide
Catir, Mustafa,Kilic, Hamdullah
, p. 1319 - 1322 (2010)
Oxidation of benzylic and allylic substrates with a bis(trifluoroacetoxyiodo)benzene/tert-butyl hydroperoxide system to the corresponding ,-unsaturated enones was investigated. The scope and reaction mechanism are discussed. Georg Thieme Verlag Stuttgart New York.
Oxidative Decarboxylation of Propiolic Acids
Cohen, Mark J.,McNelis, Edward
, p. 515 - 518 (1984)
The combination of iodine and iodine pentoxide in methanol was used to convert phenylpropiolic acid and 2-hexynoic acid to the corresponding ketal esters of one less carbon.In both cases, iodoacetylenic compounds were shown to be intermediates.In the case of the phenylpropiolic acid, a diiodoalkene was isolated and shown to be a second intermediate.
Novel effect of zinc nitrate/vanadyl oxalate for selective catalytic oxidation of α-hydroxy esters to α-keto esters with molecular oxygen: An in situ ATR-IR study
Ju, Yongwei,Du, Zhongtian,Xiao, Chuhong,Li, Xingfei,Li, Shuang
, (2019)
Selective oxidation of α-hydroxy esters is one of the most important methods to prepare high value-added α-keto esters. An efficient catalytic system consisting of Zn(NO3)2/VOC2O4 is reported for catalytic oxidation of α-hydroxy esters with molecular oxygen. Up to 99% conversion of methyl DL-mandelate or methyl lactate could be facilely obtained with high selectivity for its corresponding α-keto ester under mild reaction conditions. Zn(NO3)2 exhibited higher catalytic activity in combination with VOC2O4 compared with Fe(NO3)3 and different nitric oxidative gases were detected by situ attenuated total reflection infrared (ATR-IR) spectroscopy. UV-vis and ATR-IR results indicated that coordination complex formed in Zn(NO3)2 in CH3CN solution was quite different from Fe(NO3)3; it is proposed that the charge-transfer from Zn2+ to coordinated nitrate groups might account for the generation of different nitric oxidative gases. The XPS result indicate that nitric oxidative gas derived from the interaction of Zn(NO3)2 with VOC2O4 could be in favor of oxidizing VOC2O4 to generate active vanadium (V) species. It might account for different catalytic activity of Zn(NO3)2 or Fe(NO3)3 combined with VOC2O4. This work contributes to further development of efficient aerobic oxidation under mild reaction conditions.
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.
Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
Ece, Hamdiye,Tange, Yuji,Yurino, Taiga,Ohkuma, Takeshi
, p. 935 - 939 (2021/02/22)
3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.
Preparation method for rapidly generating alpha-ketone ester through iodine-mediated alpha-diazonium ester oxidation
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Paragraph 0025; 0028-0029, (2021/07/24)
The invention relates to the field of research of ketone ester compounds, in particular to a preparation method for rapidly generating alpha-ketone ester through iodine-mediated alpha-diazo ester oxidation, the preparation method comprises the following steps: in an organic solvent, stirring alpha-diazo ester and iodine elementary substance as raw materials at room temperature for about half an hour to obtain the alpha-ketone ester compound. According to the method, transition metal does not need to be used as a catalyst, a strong oxidant does not need to be used, only under the room temperature condition, the low-toxicity and cheap iodine elementary substance is used as the oxidant, and the alpha-keto ester is generated through efficient oxidation of the alpha-diazonic acid ester. The method has the advantages that the reaction time is short (about 0.5 hour), the universality is high, the alpha-diazonic acid ester with electron donating groups or electron withdrawing groups can achieve medium to excellent yield (80%-99%), a greener alternative approach is represented, and a new general synthesis route is provided for efficient preparation of alpha-ketoester.
