- O-hydroxyketoxime compound as well as preparation method and application thereof
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The invention relates to an o-hydroxyketoxime compound as well as a preparation method and application thereof. The o-hydroxyketoxime compound has a structural formula as shown in a formula (I) or a formula (II) which is described in the specification. The o-hydroxyoxime compound provided by the invention has adjacent hydroxyl group and oxime group structures, forms a specific hydrophobic structure with R1, R2 and R3 groups, has better chelating ability to metal ions, has particularly excellent chelating ability to Cu (II), and is excellent in flotation effect; and compared with salicylaldoxime, the recovery rate of the compound of the invention is increased by 1-30%, and the compound can be widely applied to flotation of copper oxide.
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Paragraph 0088-0091
(2022/03/18)
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- Preparation method of photoinitiator
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The invention discloses a preparation method of a photoinitiator. The preparation method comprises the following steps: acid chloride required for Fries reaction, aluminum trichloride and a solvent are mixed and then subjected to a Fourier reaction with benzene. Fries reaction intermediate purification method The Fourier reaction intermediate is mixed with chlorine for chlorination reaction, and the product of the chlorination reaction is subjected to gas-liquid separation to separate the gas. Reaction Section Step and The product purification step results in a photoinitiator finished product. To the technical scheme of the invention, the advantages of the traditional process of producing the photoinitiator are combined with the characteristics of the microchannel reactor to realize continuous preparation, the productivity can be improved, the production risk is reduced, the manpower and equipment investment are reduced, and the cost is further reduced.
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Paragraph 0074-0105
(2021/10/13)
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- Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
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The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
- Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
-
supporting information
p. 6648 - 6653
(2021/09/08)
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- Synthesis method of photoinitiator 1-hydroxycyclohexyl phenyl ketone
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The invention aims to solve the technical problems of an existing alpha-hydroxycyclohexyl phenyl ketone synthesis method, provides a synthesis method of a photoinitiator 1-hydroxycyclohexyl phenyl ketone, and belongs to the technical field of chemical synthesis. The synthesis method comprises the following steps: (1) reacting a halogenated benzene with magnesium particles to prepare a Grignard reagent, dropwise adding cyclohexylcarbonitrile into the prepared Grignard reagent, and after the reaction is completed, hydrolyzing to generate cyclohexyl phenyl ketone; and (2) reacting cyclohexyl phenyl ketone with chlorine to obtain 1-chlorocyclohexyl phenyl ketone, and carrying out a hydrolysis reaction on the 1-chlorocyclohexyl phenyl ketone and a sodium hydroxide aqueous solution under the action of a catalyst to obtain 1-hydroxycyclohexyl phenyl ketone. The method is simple in synthesis process, high in yield and suitable for industrial production.
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Paragraph 0023-0028
(2020/12/05)
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- Method for preparing alpha-hydroxy ketone photoinitiator in microreactor
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The invention relates to a method for preparing an alpha-hydroxy ketone photoinitiator in a microreactor. The method comprises the following steps: introducing chlorine into isobutyryl benzene servingas a raw material to obtain an intermediate chloroisobutyryl chloride, and carrying out alkaline hydrolysis on the intermediate under the action of an aqueous sodium hydroxide solution to obtain thealpha-hydroxy ketone photoinitiator. The preparation method of the alpha-hydroxy ketone photoinitiator has the advantages of high operation safety, high selectivity, small reaction volume, short reaction time, low equipment corrosion, low energy consumption and environment friendliness, and is a process method suitable for industrial production.
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Paragraph 0024; 0025; 0030; 0031
(2020/05/05)
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- Preparation method of photoinitiator 184
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The invention relates to a preparation method of a photoinitiator 184, in particular to the preparation of the photoinitiator 184 from 1-halocyclohexyl phenyl ketone through a hydrolysis reaction in the presence of quaternary ammonium base. By the preparation method, provided by the invention, the reaction is clean, recrystallization purification can be directly performed, and a qualified productcan be prepared; the occurrence of side reactions is avoided or reduced, the yield is increased, and the preparation method is suitable for industrial production in terms of cost and operation.
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Paragraph 0029-0032; 0035-0042
(2019/04/04)
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- Preparation method of alpha-hydroxyketone photoinitiator
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The invention provides a preparation method of an alpha-hydroxyketone photoinitiator. The preparation method comprises the steps of taking a ketone compound and a trihalomethyl-substituted benzene anda derivative thereof as raw materials, enabling the raw materials to react under the action of a polar solvent and a metal catalyst to form a halogenated intermediate in one step, and hydrolyzing theobtained product under the action of an alkali metal hydroxide aqueous solution and a phase transfer catalyst to obtain the alpha-hydroxyketone photoinitiator. The operation is simple, the reaction step is short, no Lewis acid catalyst is used in the reaction, the pollution is small, the catalyst can be recycled, by-products are less, the cost is low, and a variety of products can be produced bythe same method.
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Paragraph 0040-0042
(2019/07/04)
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- Directed Hydroxylation of sp2 and sp3 C-H Bonds Using Stoichiometric Amounts of Cu and H2O2
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The use of copper for C-H bond functionalization, compared to other metals, is relatively unexplored. Herein, we report a synthetic protocol for the regioselective hydroxylation of sp2 and sp3 C-H bonds using a directing group, stoichiometric amounts of Cu and H2O2. A wide array of aromatic ketones and aldehydes are oxidized in the carbonyl γ-position with remarkable yields. We also expanded this methodology to hydroxylate the β-position of alkylic ketones. Spectroscopic characterization, kinetics, and density functional theory calculations point toward the involvement of a mononuclear LCuII(OOH) species, which oxidizes the aromatic sp2 C-H bonds via a concerted heterolytic O-O bond cleavage with concomitant electrophilic attack on the arene system.
- Trammell, Rachel,D'Amore, Lorenzo,Cordova, Alexandra,Polunin, Pavel,Xie, Nan,Siegler, Maxime A.,Belanzoni, Paola,Swart, Marcel,Garcia-Bosch, Isaac
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supporting information
p. 7584 - 7592
(2019/06/11)
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- Ultrasonic preparation method for alpha-hydroxyketones
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The invention relates to the technical field of organic synthesis, and concretely relates to an ultrasonic preparation method for alpha-hydroxyketones. Ketones and peroxide which are used as raw materials undergo an ultrasonic reaction in the presence of an organic solvent to prepare the alpha-hydroxyketones. The preparation method provided by the invention avoids the use of halogens with high toxicity and high risks in the reaction process to avoid the risk of the product not meeting the requirements of the regulations due to the introduction of the halogens in the reaction process, and alsohas the advantages of low cost of the overall process, shortening of the cycle of batch production, simplicity in process operation and easiness in achieving of large-scale production.
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Paragraph 0032-0035
(2019/05/11)
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- Photocatalytic synthesis method of 1-hydroxyl cyclohexyl phenyl ketone compound and application thereof
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A photocatalytic synthesis method of a 1-hydroxyl cyclohexyl phenyl ketone compound comprises the following steps that (a) 4-Ryl benzaldehyde and cyclohexane produce free radical reaction under the irradiation of an ultraviolet lamp to obtain 4-Ryl cyclohexyl phenyl ketone; (b) the 4-Ryl cyclohexyl phenyl ketone uses dimethyl sulfoxide as a solvent, uses hydrobromic acid as a bromine source, hydroxyl substitution is performed to obtain 1-hydroxyl cyclohexyl-(4-R phenyl) ketone, and the dimethyl sulfoxide is removed for recycle through distillation. A 1-hydroxyl cyclohexyl-(4-R phenyl) ketone coarse product is obtained through a crystallization method, and a 1-hydroxyl cyclohexyl-(4-R phenyl) ketone photoinitiator finished product is obtained through recrystallization. The synthesis methodhas the advantages that the synthesis steps of the method are simple, the preparation cost is low and no pollution is produced. The prepared cyclohexyl phenyl ketone compound is suitable for the efficient photoinitiator of UV light curing system, the product has better non-yellowing characteristic under the irradiation of an ultraviolet source, and popularization and development of a UV light curing technology are facilitated.
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Paragraph 0019; 0020
(2019/03/08)
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- Expedient preparation of active pharmaceutical ingredient ketamine under sustainable continuous flow conditions
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A robust three-step continuous flow procedure is presented for the efficient and sustainable preparation of active pharmaceutical ingredient ketamine. The procedure relies on the main assets of continuous flow processing, starts from commercially available chemicals, utilizes low toxicity reagents and a FDA class 3 solvent under intensified conditions. The procedure features a unique hydroxylation step with molecular oxygen, a fast imination relying on triisopropyl borate and a thermolysis employing Montmorillonite K10 as a heterogeneous catalyst, all three steps being performed in ethanol. The three individual steps can be run independently or can be concatenated, thus providing a compact yet efficient setup for the production of ketamine. The scalability of the critical hydroxylation step was assessed in a commercial pilot continuous flow reactor. The process can also be adapted for the preparation of ketamine analogs. A thorough computational study on the backbone rearrangement of the cyclopentylphenylketone scaffold under thermal stress rationalizes the experimental selectivity and the various experimental observations reported herein.
- Kassin, Victor-Emmanuel H.,Gérardy, Romaric,Toupy, Thomas,Collin, DIégo,Salvadeo, Elena,Toussaint, Fran?ois,Van Hecke, Kristof,Monbaliu, Jean-Christophe M.
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supporting information
p. 2952 - 2966
(2019/06/18)
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- Synthetic method of photoinitiator 1-hydroxycyclohexyl phenyl ketone
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The invention discloses a synthetic method of a photoinitiator 1-hydroxycyclohexyl phenyl ketone. The synthetic method comprises the following steps: enabling cyclohexanecarboxylic acid chloride and benzene to be subjected to electrophilic substitution reaction under the catalysis of Lewis acid to obtain cyclohexyl phenyl ketone; enabling the cyclohexyl phenyl ketone to react with hydrogen peroxide and a hydrochloric acid solution under the action of a molecular sieve catalyst to obtain 1-chlorocyclohexyl phenyl ketone; and enabling the 1-chlorocyclohexyl phenyl ketone and a sodium hydroxide aqueous solution to be subjected to hydrolysis reaction under the action of the catalyst to obtain the 1-hydroxycyclohexyl phenyl ketone. The synthetic method disclosed by the invention has the advantages that the raw materials are cheap, easily-available, safe and environmentally friendly; hydrogen chloride produced by electrophilic substitution reaction of acyl chloride under the catalysis of Lewis acid is fully utilized and recycled, thereby reducing the discharge of waste acid water and being friendly to the environment; and selective chlorination and hydrolysis are completed in the same reactor, the operation is simple, the loss is less, and the yield is high.
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Paragraph 0015; 0017; 0018; 0020
(2019/08/12)
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- Preparation method of compound
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The invention discloses a preparation method of a hydroxyalkyl phenyl ketone compound. The preparation method comprises the steps: enabling a reactant shown in formula (II) or formula (II') to react with a cyano-containing compound shown in formula (III) in an organic solvent. The preparation method provided by the invention is relatively high in yield.
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Paragraph 0061; 0062; 0064; 0087
(2018/07/07)
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- Preparation process of photoinitiator 184
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The invention provides a preparation process of a photoinitiator 184 (1-hydroxycyclohexyl phenyl ketone). The preparation process comprises the following steps: a high-temperature ketone preparation working section; performing liquefying and mixing on benzoic acid and heptanaphthenic acid to obtain a reaction mixed solution; pre-heating the reaction mixed solution and then enabling the reaction mixed solution to react with a metal salt catalyst; preparing the ketone through dehydration and carbon dioxide removal at a high temperature (300 to 500 DEG C) to obtain benzoylcyclohexane; a one-pot process chlorinating alkaline hydrolysis working section; performing one-pot process chlorination and alkaline hydrolysis reaction by using benzoylcyclohexane, carbon tetrachloride and sodium hydroxideas regents and tetrabutyl ammonium bromide as a phase transfer catalyst so as to prepare 1-hydroxycyclohexyl phenyl ketone. The preparation process disclosed by the invention has the advantages of high selectivity, safety and environmental protection.
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Paragraph 0031; 0034; 0035; 0038; 0039; 0040; 0043
(2019/01/07)
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- Alpha-hydroxy ketone photoinitiator preparation method
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The invention relates to an alpha-hydroxy ketone photoinitiator preparation method and specifically relates to a method of utilizing ketone as a raw material to react with hydrogen peroxide under microwave radiation to prepare an alpha-hydroxy ketone photoinitiator. According to the preparation method disclosed by the invention, halogen with strong toxicity and large danger is avoided in a reaction process, and the risk that a product cannot comply with laws and regulations as the halogen is introduced in the reaction process is avoided; meanwhile, the whole technology has the advantages of low cost, simple technological operation and easiness in achieving industrial production.
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Paragraph 0016
(2018/04/03)
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- PROCESS FOR THE PREPARATION OF ALPHA-FUNCTIONALIZED KETONES
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The present invention refers to a process for the preparation of an α-functionalized ketone, an α-functionalized ketone obtained by said process, a photopolymerizable composition comprising the α-functionalized ketone and at least one photopolymerizable unsaturated compound, a method of preparing an article, an article obtained by said method, as well as the use of the α-functionalized ketone or the photopolymerizable composition as photoinitiator.
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Page/Page column 44
(2018/11/22)
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- PROCESS FOR PREPARING ARYL KETONE
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A process for preparing aryl ketones is disclosed. The process includes photo-oxidizing a compound of formula (V), (VI), (VII) or (VIII): in the presence of an oxidative system comprising at least one bromide compound to form aryl ketones. X1, X2, R1, R2, R3, L1, L2, L3, L4, t, n, m and p have the meanings as described in the specification and claims.
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- Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions
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A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.
- Liang, Yu-Feng,Jiao, Ning
-
supporting information
p. 548 - 552
(2014/01/23)
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- ENVIRONMENTALLY-FRIENDLY NEW OXIDATION PROCESS FOR CONVERTING ARYL-1,2-DIOL TO KETONE
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The present invention relates to the technical field of radiation curing photopolymerization initiator, and particularly to an environmentally-friendly new oxidation process for converting several specific aryl-1,2-diol compounds to corresponding arylhydroxyketones.
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Paragraph 0024; 0025; 0026; 0027; 0028
(2013/11/19)
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- PROCESS FOR THE PREPARATION OF AROMATIC ALPHA-HYDROXY KETONES
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Process for the preparation of aromatic alpha-hydroxyketones (aromatic α-hydroxyketones) that does not require the use of chlorine, sulfuryl chloride or bromine and comprises the halogenation of an intermediate aromatic ketone with a hydrogen halide in the presence of an oxidising compound.
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- PROCESS FOR THE PREPARATION OF AROMATIC ALPHA-HYDROXY KETONES
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Process for the preparation of aromatic alpha-hydroxyketones (aromatic α- hydroxyketones) that does not require the use of chlorine, sulfuryl chloride or bromine and comprises the halogenation of an intermediate aromatic ketone with a hydrogen halide in the presence of an oxidising compound.
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Page/Page column 18
(2010/01/29)
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- Lithographic printing method
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A lithographic printing plate precursor comprising a support and an image-recording layer containing at least one infrared absorbing agent of a cyanine dye in which a HOMO energy level of each of substituents present on both terminal nitrogen atoms is -10.0 eV or higher. An infrared absorbing agent of a cyanide dye represented by formula (V) shown below: wherein Z 1 and Z 2 each independently represents an aromatic ring which may have a substituent or a hetero aromatic ring which may have a substituent; R 10 and R 20 each independently represents a phenyl group, a naphtyl group, an anthracenyl group, a carbazolyl group or a phenothiazinyl group each of which may have a substituent; A - represents an anion which exists in case of being necessary for neutralizing a charge and is selected from a halogen ion, a perchlorate ion, a tetrafluoroborate ion, a hexafluorophosphate ion and a sulfonate ion; and n represents 1 or 2.
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- PREPARATION OF ALPHA-HYDROXYKETONES
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A process for the preparation of an 1, 1 -disubstituted oxirane is disclosed, wherein an organic sulphide is reacted in a polar solvent with an educt containing a leaving group attached to a primary or secondary carbon atom, and/or the sulfonium salt formed in this way is reacted with a ketone in presence of a base and a polar solvent. Oxiranes of the type obtained may be further converted into the corresponding α-hydroxyketone or α-aminoketone, either in one step by subjecting to aerobic oxidation in the presence of a transition metal catalyst, or in two steps by hydrolyzation in the presence of an aqueous acid to the corresponding dialcohol and subsequent selective oxidation. Further described are some novel epoxide intermediates. The α-hydroxyketones and α-aminoketones thus obtainable are useful inter alga as photoinitiators.
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- Dihydroquinolines as novel n-NOS inhibitors
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Dihydroquinolines have been synthesized and have been shown to be potent n-NOS inhibitors. Selectivity versus e-NOS was increased to approximately 100-fold through appropriate substitution at the benzene ring.
- Jaroch, Stefan,Hoelscher, Peter,Rehwinkel, Hartmut,Suelzle, Detlev,Burton, Gerardine,Hillmann, Margrit,McDonald, Fiona M.
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p. 2561 - 2564
(2007/10/03)
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- Conversion of α,β-unsaturated ketones into α-hydroxy ketones using an Mn(III) catalyst, phenylsilane and dioxygen: Acceleration of conjugate hydride reduction by dioxygen
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Treatment of a variety of α,β-unsaturated ketones with Mn(dpm)3 (3 mol%)/PhSiH3 (1.3 equiv.)/isopropyl alcohol/O2, followed by reductive work-up with P(OEt)3 resulted in the formation of α-hydroxy-ketones. (C) 2000 Elsevier Science Ltd.
- Magnus,Payne,Waring,Scott,Lynch
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p. 9725 - 9730
(2007/10/03)
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- Molecular complex compounds of acylphosphine oxide and α-hydroxy ketones as photoinitiators
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Molecular complex compounds comprising a mono-, bis- or trisacylphosphine oxide compound with an α-hydroxy ketone compound are suitable as photoinitiators for the photopolymerization of free-radically polymerizable compounds.
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- Conversion of ketone trimethylsilylcyanohydrins to several types of compounds
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Cyclic ketone O-trimethylsilylcyanohydrins (2) were prepared and converted to various compounds: α-hydroxyketones (3), dehydroxylated ketones (4), α,β-unsaturated ketones (9), tricyclic ketones (10), 1-ethoxycarbonyl-4- phenyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphthalenone (13), 1- phenylperhydroisocoumarin (18) and 1,2,3,4,4a,10,11,11a-octahydro-5h- benzo[a,d]cyclohepten-10-one (20).
- Ohta,Yamashita,Arita,Kajiura,Kawasaki,Noda,Izumi
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p. 1294 - 1301
(2007/10/02)
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- Reductive Coupling of Benzoyl Cyanide and Carbonyl Compounds by Aqueous Ti(III) Ions. A New Convenient and Selective Access to the Less Stable Mixed Benzoins
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The reactive species formed by the Ti(III) ion reduction of benzoyl cyanide (1) adds to the C-atom of carbonyl compounds 2 under simple experimental conditions.The intermediate 1,2-diols 3 are smoothly converted, without isolation, into the less thermodynamically stable mixed benzoins 4, which are not accessible by the classical benzoin condensation.The possible mechanisms involved in the reaction are discussed.
- Clerici, Angelo,Porta, Ombretta
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p. 2889 - 2893
(2007/10/02)
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- Trifluoromethanesulfonic (Triflic) Acid Catalyzed Transformations of α-Hydroxy Carbonyl Compounds
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Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantanone.Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione.Reactions of a series of α-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively.The reactions and their suggested mechanism are discussed.
- Olah, George A.,Wu, An-hsiang
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p. 2531 - 2534
(2007/10/02)
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- ADDITION OF GRIGNARD REAGENTS TO O-TRIMETHYLSILYLATED CYANOHYDRINS: SYNTHESIS OF ACYLOINS
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Grignard reagents have been found to react readily with O-trimethylsilylated cyanohydrins to afford, after acid hydrolysis of intermediates, good yields of acyloins.
- Krepski, Larry R.,Heilmann, Steven M.,Rasmussen, Jerald K.
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p. 4075 - 4078
(2007/10/02)
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- FLUORIDE-CATALYZED CONVERSION OF ACYLSILANES TO ALDEHYDES AND KETONES
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Acylsilanes undergo efficient protodesilylation upon treatment with fluoride ion in moist DMSO, HMPT, or THF.The reaction is also catalyzed by methoxide ion in methanol or DMSO, but not by chloride ion or bromide ion.Fluoride-catalyzed desilylation in the presence of alkyl halides, aldehydes, or ketones results in modest yields of the corresponding alkylated products.
- Schinzer, Dieter,Heathcock, Clayton H.
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p. 1881 - 1884
(2007/10/02)
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- α-HETEROSUBSTITUTED PHOSPHONATE CARBANIONS IX : DIETHYL 1-PHENYL-1-TRIMETHYLSILOXYMETHANE PHOSPHONATE AS AN ACYL ANION EQUIVALENT; A NOVEL METHOD FOR THE PREPARATION OF α-HYDROXYKETONES.
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Diethyl 1-phenyl-1-trimethylsiloxymethane phosphonate carbanion was found to react as an effective acyl anion equivalent in the preparation of α-hydroxy ketones from aliphatic and aromatic aldehydes and ketones.A 1,4-oxygen-oxygen silicon migration was also observed.
- Koenigkramer, Rusty E.,Zimmer, Hans
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p. 1017 - 1020
(2007/10/02)
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