10458-14-7Relevant articles and documents
Oxidation of alcohols to aldehydes and ketones using TBHP as an oxidant over LaMO3 (M = Cr, Mn, Co, Ni, Fe) perovskites
Singh, Savita J.,Jayaram, Radha V.
, p. 299 - 308 (2012)
Oxidation of a wide variety of structurally and electronically diverse primary and secondary alcohols to aldehydes and ketones was carried out using a novel catalytic system of LaCrO3 and tert-butyl hydroperoxide (TBHP) under solvent-free conditions. The methodology afforded the desired carbonyl compounds in good to excellent yields, and the catalyst can be reused several times with no significant loss in activity. Copyright Taylor & Francis Group, LLC.
Chromium trioxide on H-Y zeolite: Rapid oxidation of alcohols to carbonyl compounds in solventless system using microwaves
Mirza-Aghayan, Maryam,Heravi, Majid M.
, p. 785 - 789 (1999)
In an environmentally benign solventless system, alcohols are rapidly oxidized to carbonyl compounds using HY-zeolite supported chromium trioxide as an oxidant under microwave irradiation.
Intramolecular hydrogen transfer reaction: Menthon from isopulegol
Schaub, Thomas,Ruedenauer, Stefan,Weis, Martine
, p. 2575 - 2577 (2014)
The flavor menthon (isomeric mixture of (-)-menthon and (+)-isomenthon) was obtained in good yields and selectivities by a solventless ruthenium catalyzed isomerization of the homoallylic alcohol (-)-isopulegol. In contrast to most previous assumptions on such isomerization reactions, this reaction follows an intermolecular pathway, with menthol and pulegon being the central intermediates in this transformation.
Oxidation of Benzylic and Secondary Alcohols to Carbonyl Compounds by NaBrO3-NH4Cl Reagent in Aqueous Acetonitrile
Shaabani, Ahmad,Ameri, Majid
, p. 100 - 101 (1998)
NaBrO3 combined with NH4Cl is found to be an efficient reagent for the conversion, in aqueous acetonitrile and under mild conditions, of benzylic and secondary alcohols into aldehydes and ketones, respectively.
Preparation and Use of Tetra-n-butylammonium Per-ruthenate (TBAP reagent) and Tetra-n-propylammonium Per-ruthenate (TPAP reagent) as New Catalytic Oxidants for Alcohols
Griffith, William P.,Ley, Steven V.,Whitcombe, Gwynne P.,White, Andrew D.
, p. 1625 - 1627 (1987)
Tetra-n-butylammonium per-ruthenate (Bun4N)(RuO4) and tetra-n-propylammonium per-ruthenate (Prn4N)(RuO4), with N-methylmorpholine N-oxide, function as mild catalitic oxidants for the high yield conversion of alcohols to aldehydes and ketones and are competitive with more conventional reagents.
OXYDATION D'ALCOOLS PAR L'ANHYDRIDE CHROMIQUE DANS LES CONDITIONS DU TRANSFERT DE PHASE SOLIDE-LIQUIDE.
Gelbard, Georges,Brunelet, Thierry,Jouitteau, Catherine
, p. 4653 - 4654 (1980)
Catalytic amounts quaternary ammonium salts afforded efficient oxidation of alcohols by chromium trioxide at room temperature in organic solvents.
Pd(II)-hydrotalcite-catalyzed selective oxidation of alcohols using molecular oxygen
Uemura,Kakiuchi,Nishimura,Inoue
, p. 165 - 172 (2001)
A novel heterogenized Pd catalyst, Pd supported by hydrotalcite [Pd(II)-hydrotalcite], was synthesized by a simple operation from commercially available hydrotalcite, Pd(OAc)2 and pyridine. The catalyst was effective for the oxidation of a wide range of alcohols using molecular oxygen as a sole oxidant. With this catalytic system, various alcohols were readily converted to the corresponding aldehydes or ketones selectively in high to excellent yields. Sterically less hindered substrates were converted to the corresponding ketones much faster than the hindered ones. For example, cyclohexanol was converted to cyclohexanone in 79% yield for 15 hr, while larger-sized cyclic alcohols were oxidized to the corresponding ketones only in 32-77% yields in the same reaction time. The catalyst was also applicable to the oxidation of unsaturated alcohols such as geraniol and nerol without any isomerization of an alkenic part. Modified Pd(II)-hydrotalcite [Pd(II)-hydrotalcite(m)] could be reused several times while keeping its activity.
1-Methyl-3-butylimidazolium decatungstate in ionic liquid: An efficient catalyst for the oxidation of alcohols
Chhikara, Bhupender S.,Tehlan, Sarita,Kumar, Anil
, p. 63 - 66 (2005)
An excellent system for the selective oxidation of benzylic and secondary alcohols with hydrogen peroxide catalyzed by 1-methyl-3-butylimidazolium decatungstate in [bmim][BF4] ionic liquid is described. The catalytic system is reusable and products are obtained in excellent yield under environmentally benign conditions.
ULTRASONICALLY IMPROVED REDUCTIVE PROPERTIES OF AN AQUEOUS Zn-NiCl2 SYSTEM - 1 SELECTIVE REDUCTION OF α,β-UNSATURATED CARBONYL COMPOUNDS
Petrier, Christian,Luche, Jean-Louis
, p. 2347 - 2350 (1987)
Conjugate addition of several compounds is obtained with good to excellent yield in an aqueous medium using a reagent constituted by zinc dust and nickel chloride(9-1).Ultrasounds are shown to improve the yields and reaction rates.
Novel Vanadium-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones under Atmospheric Oxygen
Velusamy, Subbarayan,Punniyamurthy
, p. 217 - 219 (2004)
(Matrix presented) Oxidation of alcohols to aldehydes and ketones has been studied in high yields using atmospheric oxygen and a catalytic amount of V 2O5 in toluene under heating (ca. 100°C). Secondary alcohols can be chemoselectively converted into ketones in the presence of primary hydroxy groups.
Transition-metal- and organic-solvent-free: A highly efficient anaerobic process for selective oxidation of alcohols to aldehydes and ketones in water
Gogoi, Pranjal,Konwar, Dilip
, p. 3473 - 3475 (2005)
A new system, I2-KI-K2CO3-H2O, selectively oxidized alcohols to aldehydes and ketones under anaerobic condition in water at 90°C with excellent yields. The process is green, mild and inexpensive. The Royal Society of Chemistry 2005.
Efficient ruthenium-catalyzed aerobic oxidation of alcohols using a biomimetic coupled catalytic system
Csjernyik, Gabor,Ell, Alida H.,Fadini, Luca,Pugin, Benoit,Baeckvall, Jan-E.
, p. 1657 - 1662 (2002)
Efficient aerobic oxidation of alcohols was developed via a biomimetic catalytic system. The principle for this aerobic oxidation is reminiscent of biological oxidation of alcohols via the respiratory chain and involves selective electron/proton transfer. A substrate-selective catalyst (ruthenium complex 1) dehydrogenates the alcohol, and the hydrogens abstracted are transferred to an electron-rich quinone (4b). The hydroquinone thus formed is continuously reoxidized by air with the aid of an oxygen-activating Co-salen type complex (6). Most alcohols are oxidized to ketones in high yield and selectivity within 1-2 h, and the catalytic system tolerates a wide range of O2 concentrations without being deactivated. Compared to other ruthenium-catalyzed aerobic oxidations this new catalytic system has high turnover frequency (TOF).
Direct oxidative deprotection of tetrahydropyranyl ethers using hexamethylenetetramine-bromine supported onto silica gel under microwave irradiation in solventless system
Dehkordi, Mahboobeh Behnam,Heravi, Majid M.,Ziafati, Ahmad,Khosrofar, Parviz,Ghassemzadeh, Mitra
, p. 1493 - 1496 (2004)
Primary and secondary tetrahydropyranyl ethers (THP ethers) are converted to their corresponding carbonyl compounds efficiently using hexamethylene- tetramine-bromine supported onto silica gel under microwave irradiation in solvent-free conditions.
Hexamethylenetetrammonium fluorochromate. A new reagent for oxidation of organic substrates
Turunc, Ersan,Aydin, Fatma
, p. 363 - 366 (2004)
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Oxidative Deprotection of Tetrahydropyranyl Ethers to Carbonyl Compounds with Montmorillonite K-10 Supported Bis(trimethylsilyl) Chromate under Non-aqueous Conditions
Heravi, Majid M.,Ajami, Dariush
, p. 718 - 719 (1998)
A variety of tetrahydropyranyl ethers are oxidized to the corresponding carbonyl compounds in excellent yields by montmorillonite K-10 supported bis(trimethylsilyl) chromate in dichloromethane at room temperature.
New biobased tetrabutylphosphonium ionic liquids: Synthesis, characterization and use as a solvent or co-solvent for mild and greener Pd-catalyzed hydrogenation processes
Hayouni, Safa,Robert, Anthony,Ferlin, Nadège,Amri, Hassen,Bouquillon, Sandrine
, p. 113583 - 113595 (2016)
Phosphonium-based Ionic Liquids (PhosILs) with natural organic derived anions (l-lactate, l-tartrate, malonate, succinate, l-malate, pyruvate, d-glucuronate, d-galacturonate, ferulate, p-coumarate) were easily prepared by acid-base method from tetrabutylphosphonium hydroxide and an excess of the corresponding acid with good yields. Their characterization was realized through classical NMR, IR and elemental analysis techniques; their viscosity and ATG parameters were also determined. These ionic liquids showed good performance and recyclability in the selective Pd-catalyzed hydrogenation of alkenes, polyenes like linoleic acid and enantioselective hydrogenation of unsaturated ketones such as isophorone at room temperature under atmospheric H2 pressure. Furthermore, NMR studies leading to computational calculations were performed to establish easily the composition of the resulting mixture obtained through the hydrogenation of linoleic acid.
Oxidation of Secondary Alcohols over Hydrous Zirconium(IV) Oxide
Kuno, Hideyuki,Takahashi, Kyoko,Shibagaki, Makoto,Shimazaki, Kazuko,Matsushita, Hajime
, p. 1943 - 1946 (1990)
The oxidation of secondary alcohols with ketones was carried out by catalysis with hydrous zirconium(IV) oxide.In the batch reaction system, the oxidation proceeded efficiently to give the corresponding ketones, except for some secondary alcohols.On the other hand, all of the secondary alcohols were efficiently converted to the corresponding ketones in the flow oxidation system.The influence of the hydrogen acceptor on the oxidation rate was investigated by the use of several ketones, and the oxidation rate was influenced by the electron density and steric hindrance around the carbonyl group.The dependence on the reaction temperature was also investigated in the flow reaction system.
Nicotinamide-dependent Ene reductases as alternative biocatalysts for the reduction of activated alkenes
Durchschein, Katharina,Wallner, Silvia,MacHeroux, Peter,Schwab, Wilfried,Winkler, Thorsten,Kreis, Wolfgang,Faber, Kurt
, p. 4963 - 4968 (2012)
Four NAD(P)H-dependent non-flavin ene reductases have been investigated for their ability to reduce activated C=C bonds in an asymmetric fashion by using 20 structurally diverse substrates. In comparison with flavin-dependent Old Yellow Enzyme homologues, a higher degree of electronic activation was required, because the best activities were obtained with enals and nitroalkenes rather than enones and carboxylic esters. Although FaEO from Fragaria x ananassa (strawberry) and its homologue SlEO from Solanum lycopersicum (tomato) exhibited a narrow substrate spectrum, progesterone 5β-reductase (At5β-StR) from Arabidopsis thaliana (thale cress) and leukotriene B4 12-hydroxydehydrogenase (LTB4DH/PGR) from Rattus norvegicus (rat) appear to be promising candidates, in particular for the asymmetric bioreduction of open-chain enals, nitroalkenes and α,β-unsaturated γ-butyrolactones. Competing nitro reduction and non-enzymatic Weitz-Scheffer epoxidation were largely suppressed. Electronically activated alkenes have been stereoselectively reduced by using a single-enzyme-cofactor system employing nicotinamide-dependent non-flavin ene reductases. Copyright
A versatile method for the hydrogen peroxide oxidation of alcohols using PTC condition in tert-butanol
Chhikara, Bhupender S.,Chandra, Ramesh,Tandon, Vibha
, p. 872 - 874 (2005)
An efficient protocol for the oxidation of secondary and primary alcohols to the corresponding ketones and aldehydes and/or carboxylic acids using hydrogen peroxide as oxidant is described. A quasi-homogenous reaction system was obtained by t-butanol as solvent to achieve high yield of the product in short time.
Preparation and reactivity of 1,3,5,7-tetrakis[4-(diacetoxyiodo)phenyl] adamantane, a recyclable hypervalent iodine(III) reagent
Tohma, Hirofumi,Maruyama, Akinobu,Maeda, Akihisa,Maegawa, Tomohiro,Dohi, Toshifumi,Shiro, Motoo,Morita, Tetsuichiro,Kita, Yasuyuki
, p. 3595 - 3598 (2004)
A wide range of oxidative reactions are mediated by novel, nonpolymeric, and recyclable hypervalent IIII reagents (e.g. 2). In all cases, tetraiodide 1 was recovered nearly quantitatively in pure form after a simple workup. Reoxidation of 1 to
Zeofen: A user-friendly catalyst for oxidative cleavage of tetrahydropyranyl ethers under non-aqueous conditions
Mohajerani,Heravi,Ajami
, p. 871 - 873 (2001)
Primary and secondary tetrahydropyranyl ethers are efficiently converted to carbonyl compounds in excellent yields by zeofen under non-aqueous conditions.
A Novel Hexanuclear Heteropolyperoxo Oxidation Catalyst: Preparation, X-Ray Crystal Structure and Reactions of 3W6O13(O2)4(OH)2(OH2)>*4H2O
Griffith, William P.,Parkin, Bernardeta C.,White, Andrew J. P.,Williams, David J.
, p. 2183 - 2184 (1995)
The crystal structure of the title compound, 1, reveals the presence of two distinct types of tungsten atom in which the four bearing peroxo groups have distorted pentagonal-bipyramidal geometries and the remaining two are octahedral; 1 is an effective catalyst for monoalkene epoxidation, and the oxidation of primary and secondary alcohols, with H2O2 as co-oxidant.
Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones
Sales, Ayrlane,de Oliveira e Castro, Isabela Andrade,de Menezes, Frederico Duarte,Selva, Thiago Matheus Guimar?es,Vilar, Márcio
, p. 295 - 305 (2019)
The potential of cucurbit[5]uril to be used as inverse phase transfer catalyst in electrocatalytic hydrogenation of α,β-unsaturated ketones is illustrated. The interaction behavior among isophorone and cucurbit[5]uril was also investigated using cyclic voltammetry and UV/vis absorption spectroscopy. The results concerning to both techniques revealed an enhancement in the intensity of the absorption peak and also in the current cathodic peak of isophorone in presence of cucurbit[5]uril. This achievement is related to the increase of the isophorone solubility in the medium being an indicative of a host-guest complex formation. The electrochemical hydrogenation of isophorone using cucurbit[5]uril was more efficient than others well-stablish methodologies. Regarding to (R)-(+)-pulegone and (S)-(+)-carvone, the use of cucurbit[5]uril leads to an increase of 17% and 9%, on average, respectively, in the yields when compared to the control reaction. The efficiency of selective C=O bond hydrogenation of 1-acetyl-1-cyclohexene was evaluated. The presence of cucurbit[5]uril increased by 12% the hydrogenations yields of 1-acetyl-1-cyclohexene when compared to the control reaction. In this sense, these results open up an opportunity to carry out electrocatalytic reactions within the cucurbit[5]uril environment.
Oxidative deprotection of trimethylsilyl ethers with hexamethylenetetramine-bromine supported onto silica gel under microwave irradiation in solventless system
Dehkordi, Mahboobeh Behnam,Heravi, Mojid M.,Khosrofar, Parviz,Ziafat, Ahmad,Ghassemzadeh, Mitra
, p. 2595 - 2598 (2004)
Hexamethylenetetramine-bromine supported onto silica gel rapidly converts trimethylsilyl ethers to their corresponding carbonyl compounds under microwave irradiation in solventless system.
Quinoxalinium fluorochromate (QxFC): A new and efficient reagent for the oxidation of alcohols in solution, under solvent-free conditions and microwave irradiation
Sendil, Kivilcim,Oezguen, Beytiye
, p. 959 - 964 (2006)
The new mild oxidizing agent, quinoxalinium fluorochromate (QxFC), has been easily prepared by reacting quinoxaline with an aqueous solution of CrO 3 and HF. This reagent is suitable for oxidizing various primary and secondary alcohols to their corresponding carbonyl compounds and anthracene to antraquinone. The reactions were carried out in solution, under solvent-free conditions and microwave irradiation. The results show that the rates of the reactions and the yields are usually highest under microwave irradiation. Copyright Taylor & Francis Group, LLC.
(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols
Kumar, Kamlesh,Joshi, Penny,Rawat, Diwan S
, (2021/09/02)
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Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water
Dehkordi, S. Saeid Saei,Albadi, Jalal,Jafari, Abbas Ali,Samimi, Heshmat Allah
, p. 2527 - 2538 (2021/03/24)
A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.
Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl
He, Tianyu,Chen, Dengfeng,Qian, Shencheng,Zheng, Yu,Huang, Shenlin
supporting information, p. 6525 - 6529 (2021/09/02)
A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.
