- Cobalt(II) Chloride Catalysed Coupling of Acetic Anhydride with Aldehydes. A Novel Synthesis of Asymmetrical 1,2-Diones
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Cobalt(II) chloride in acetonitrile efficiently catalyses the coupling of acetic anhydride with various aldehydes to the corresponding 1,2-diones in very high yields.
- Ahmad, Saeed,Iqbal, Javed
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- Selective oxidation of aryl ketones to α-diketones with 4-aminoperoxybenzoic acid supported on silica gel in presence of air
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4-Aminoperoxybenzoic acid supported on silica gel in presence of air was found to be a selective and convenient oxidant for the oxidation of methylene groups in aryl ketones to convert them to α-diketones. Springer-Verlag 2004.
- Ghazanfari, Dadkhoda,Najafizadeh, Fariba,Khosravi, Fereshteh
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- Ozonolysis of Alkynes - A Flexible Route to Alpha-Diketones: Synthesis of AI-2
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A mild procedure for the low-temperature conversion of alkynes to diketones has been developed and employed in the synthesis of AI-2.
- Alterman, Joshua L.,Halverson, Larry J.,Kraus, George A.,Stroud, Marissa Roghair,Vang, Dua X.
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supporting information
p. 7424 - 7426
(2020/10/05)
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- Palladium-Catalyzed Synthesis of 1,2-Diketones from Aryl Halides and Organoaluminum Reagents Using tert-Butyl Isocyanide as the CO Source
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In this work, an interesting and practical procedure for the synthesis of 1,2-diketones from aryl halides and organoaluminum reagents has been developed. Employing tert-butyl isocyanide as the CO source and palladium as the catalyst, the desired 1,2-diketones were isolated in good to excellent yields with good functional group tolerance. Concerning the reaction partners, besides aryl halides, both alkyl- A nd arylaluminum reagents were all suitable substrates here.
- Chen, Bo,Wu, Xiao-Feng
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supporting information
p. 636 - 641
(2020/01/31)
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- A simple synthetic route to enantiopure α-hydroxy ketone derivatives by asymmetric hydrogenation
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High enantioselectivities (up to 99% ee) have been observed for the catalytic asymmetric hydrogenation of the α-ketone enol acetates. DuanPhos has been proved to be the most effective ligand for this reaction. The high yield and enantioselectivity of the asymmetric hydrogenation of the α-ketone enol acetates represents a feasible synthetic route to important pharmaceutical building blocks: α-hydroxy ketones. Copyright
- Sun, Tian,Zhang, Xumu
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supporting information
p. 3211 - 3215
(2013/01/15)
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- A new synthetic route for 1,2-diketo compounds using unexpected C-C bond cleavage by PCC
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An efficient method has been established for the preparation of 1,2-diketones by unexpected C-C bond cleavage in 4-keto-2-hydroxy esters using pyridiniumchlorochromate (PCC).
- Bhosale, Shrikar M.,Momin, Aadil A.,Gawade, Rupesh L.,Puranik, Vedavati G.,Kusurkar, Radhika S.
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p. 5327 - 5330
(2012/11/07)
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- New synthetic strategy for high-enantiopurity N-protected α-amino ketones and their derivatives by asymmetric hydrogenation
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Asymmetric hydrogenation of α-dehydroamino ketones catalyzed by a rhodium-chiral phosphorus ligand complex (up to 99% ee, 1000 TON), represents an efficient approach to chiral α-amino ketones. The reduction of α-amino ketones catalyzed by palladium on carbon (Pd/C) leads to amphetamine precursors with quantitative yield and no significant enantioselectivity loss.
- Sun, Tian,Hou, Guohua,Ma, Miaofeng,Zhang, Xumu
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supporting information; experimental part
p. 253 - 256
(2011/04/16)
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- Palladium-catalyzed carbonation-diketonization of terminal aromatic alkenes via carbon-nitrogen bond cleavage for the synthesis of 1,2-diketones
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A palladium-catalyzed carbonation-diketonization reaction of terminal alkenes via carbon-nitrogen bond cleavage under an atmosphere of oxygen has been developed. A series of 1,2-diketones were readily prepared from the reaction of aromatic terminal alkenes with nitroalkanes.
- Wang, Azhong,Jiang, Huanfeng,Li, Xianwei
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supporting information; experimental part
p. 6958 - 6961
(2011/10/02)
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- Reaction of Z isomers of alkylaromatic 1,2-hydroxylamino oximes with 1,2-diketones
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The reactions of Z isomers of alkylaromatic 1,2-hydroxylamino oximes containing the hydroxylamino group at the primary or secondary carbon atom with diacetyl afford 6-acetyl-5,6-dihydro-4H-1,2,5-oxadiazines. The reactions of these compounds with alkylaromatic 1,2-diketones produce N-substituted α-aroylnitrones or 6-aroyl-5,6-dihydro-4H-1,2,5-oxadiazines or, alternatively, their tautomeric mixtures.
- Amitina,Grigor'ev,Tikhonov
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p. 1046 - 1051
(2008/02/01)
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- 2-Iodoxybenzoic acid mediated facile conversion of 1,3-diols to 1,2-diketones by oxidative cleavage of the C-C bond
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1,3-Diols undergo smooth oxidative cleavage of the C-C bond in the presence of 2-iodoxybenzoic acid (IBX) affording 1,2-diketones in excellent yields under mild conditions. Georg Thieme Verlag Stuttgart.
- Yadav,Biswas, Swapan Kumar,Srinivas
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p. 4237 - 4241
(2008/09/16)
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- Selective oxidation of benzylic or allylic hydroxyl group of sec-1,2-diols
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A mild and efficient method to selectively oxidize chiral sec-1,2-diols has been developed, which demonstrates that 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) can selectively oxidize benzylic or allylic hydroxyl group of sec-1,2-diols under ultrasound wave promotion. The configuration of the adjacent chiral center is retained.
- Peng, Kun,Chen, Fuxin,She, Xuegong,Yang, Chunhui,Cui, Yuxin,Pan, Xinfu
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p. 1217 - 1220
(2007/10/03)
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- Rapid microwave-promoted solvent-free oxidation of α-methylene ketones to α-diketones
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A convenient and rapid method for the oxidation of α-methylene ketones to α-diketones has been described involving the reaction of pyridine N-oxide with α-nosyloxy ketone intermediates.
- Lee, Jong Chan,Park, Hong-Jun,Park, Jin Young
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p. 5661 - 5664
(2007/10/03)
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- Reactions and reactivity of acyloxycarbenes
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Phenylacetoxycarbene, phenyl(pivaloyloxy)carbene, and phenyl(benzoyloxy)carbene, photolytically generated from diazirine precursors in pentane at 25°C, efficiently rearranged by 1,2-acyl migrations to give high yields of the appropriate 1,2-diketones. The kinetics of these rearrangements were determined by laser flash photolysis. Substituent effects on the acyl migrations and ab initio electronic structure calculations on ground state carbenes and transition states were employed to analyze the rearrangement mechanism. Additions of phenylacetoxycarbene to alkenes proceeded in good yields, in lieu of the 1,2-acyl shift; absolute rate constants were obtained for these reactions of the ambiphilic carbene. (Phenoxymethyl)acetoxycarbene gave only a 1,2-H shift; the potentially competitive 1,2-acetyl migration was suppressed.
- Moss, Robert A.,Xue, Song,Liu, Weiguo,Krogh-Jespersen, Karsten
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p. 12588 - 12597
(2007/10/03)
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- CONVENIENT PREPARATION OF UNSYMMETRICALLY SUBSTITUTED BENZILS BY PERMANGANATE OXIDATION OF β-OXO PHOSPHORUS YLIDES
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Oxidative cleavage of a range of ylides 4 with R1 and/or R2 being aromatic groups, using KMnO4 in a two-phase system, affords unsymmetrical benzils and 1-arylpropane-1,2-diones 5 in moderate to good yield, and the ylide formation and oxidation can be combined in a convenient one-pot method.Key words: Phosphorus ylides, oxidation, 1,2-diketones, benzils, permanganate, oxoalkylidenetriphenylphosphoranes.
- Aitken, R. Alan,Cadogan, J. I. G.,Gosney, Ian
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p. 281 - 286
(2007/10/02)
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- REACTIONS OF 1-ARYL-2,2-DICHLORO-1-PROPANONES. II. REACTION OF 1-(4-R-PHENYL)-2,2-DICHLORO-1-PROPANONES WITH SOME NUCLEOPHILES
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The reactions of 1-(4-R-phenyl)-2,2-dichloro-1-propanones with alkali-metal alkoxides and certain amines (morpholine, piperidine) and also their conversion into α-diketones were studied.By IR and mass spectrometry it was shown that the methoxylation of these compounds with sodium methoxide leads to the formation of the products from direct substitution of the halogen atoms by methoxyl groups.The kinetics of methoxylation are described by a second-order equation, and a Hammett correlation with a positive reaction constant is observed in the rate constants.
- Bratchanskii, P. E.,Komissarova, G. G.,Esipov, G. V.
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p. 1961 - 1964
(2007/10/02)
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