- Unprecedented, selective Nef reaction of secondary nitroalkanes promoted by DBU under basic homogeneous conditions
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Secondary nitrocompounds can be converted into the corresponding ketones under basic conditions using DBU in acetonitrile. Primary nitroalkanes are unaffected by these conditions. Elsevier Science Ltd. All rights reserved.
- Ballini, Roberto,Bosica, Giovanna,Fiorini, Dennis,Petrini, Marino
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Read Online
- Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
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Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
- Ma, Xiaofeng,Dewez, Damien F.,Du, Le,Luo, Xiya,Markó, István E.,Lam, Kevin
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- Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
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Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
- Ma, Xiaofeng,Du, Le,Luo, Xiya,Markó, István E.,Dewez, Damien F.,Lam, Kevin
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p. 12044 - 12055
(2019/03/01)
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- Novel reactivity of N-bridged diiron phthalocyanine in the activation of C-H bonds: Hydroacylation of olefins as an example of the efficient formation of C-C bonds
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Bridge over troubled iron: An N-bridged diiron tetra-tert- butylphthalocyanine complex, usually employed for oxidation reactions, also catalyzes the addition of acetaldehyde to olefins (see scheme) to provide methylketones with a high selectivity (up to 92%) and high turnover numbers (3600-5700). Copyright
- Alvarez, Leonardo X.,Kudrik, Evgeny V.,Sorokin, Alexander B.
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supporting information; experimental part
p. 9298 - 9301
(2011/10/09)
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- Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones
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An efficient method for the N-heterocyclic carbene (NHC)-catalyzed conjugate addition of acetyl anions to various α,β-unsaturated acceptors (Stetter reaction) has been optimized by using 2,3-butandione (biacetyl) as an alternative surrogate of acetaldehyde. The disclosed procedure proved to be compatible with microwave dielectric heating for reaction time reduction and with the use of different linear α-diketones as acyl anion donors (e.g. 3,4-hexanedione for propionyl anion additions). Moreover, the unprecedented umpolung reactivity of cyclic α-diketones in the atom economic nucleophilic acylation of chalcones is herein presented. Mechanistic aspects of the thiazolium-based catalysis involving linear and cyclic α-diketone substrates are also discussed. The Royal Society of Chemistry 2011.
- Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Giovannini, Pier Paolo,Massi, Alessandro,Pacifico, Salvatore
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experimental part
p. 8437 - 8444
(2012/04/10)
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- AuBr3-catalyzed thiooxime-to-carbonyl conversion: From chiral aliphatic nitro compounds to ketones without racemization
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A new variant of the NO2-to-CO transformation (the Nef reaction) that occurs at room temperature under neutral conditions is uncovered. After the conversion of secondary nitroalkanes to phenylsulfenylketlmines, these thlooximes are hydrolyzed quantitatively In situ, In THF-H2O at pH 7, by addition of AuBr3 (but not with other MXn!). Adducts arising from asymmetric nitro-Mlchael and nltro-aldol reactions afford 1,4-dlketones and a-alkoxy ketones, respectively, with full retention of the configuration of the stereocenters a to the CHNO2/C=N-SPh/C=o groups.
- Bures, Jordi,Lsart, Carles,Vllarrasa, Jaume
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supporting information; experimental part
p. 4414 - 4417
(2009/12/24)
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- Photochemistry in supercritical carbon dioxide. The benzophenone-mediated addition of aldehydes to α,β-unsaturated carbonyl compounds
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The photo-induced addition of aldehydes to α,β-unsaturated carbonyl compounds is an effective, 'environmentally benign' method for the synthesis of 2-acyl-1,4-hydroquinones (from quinones) and 1,4-diketones (from enones). This process has been improved by eliminating benzene as a solvent and replacing it with supercritical carbon dioxide. Highest yields were obtained at higher CO2 pressures, or with the addition of 5% t-butyl alcohol as co-solvent.
- Pacut, Ryszard,Grimm, Michelle L.,Kraus, George A.,Tanko, James M
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p. 1415 - 1418
(2007/10/03)
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- Samarium diiodide-mediated pinacolization of diketones - II. Synthesis of polycyclic frameworks containing a cyclobutane-1,2-diol and a cyclopentane-1,2-diol
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The title reaction has been applied to the synthesis of a variety of polycyclic networks. Scope and limitations of the procedure are evaluated.
- Nowitzki, Olaf,Muennich, Ira,Stucke, Holger,Hoffmann
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p. 11799 - 11810
(2007/10/03)
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- Clemmensen Reduction. XI. Fragmentation Reactions of Some 3-Acetylcycloalkanones
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Clemmensen reduction of a series of 3-acetylcycloalkanones yields, as the major product, an acyclic unsaturated ketone, the product of fragmentation.Some normal carbonyl-methylene reduction also occurs.A mechanistic rationale for the fragmentation is advanced.
- Bailey, Karen E.,Davis, Brian R.
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p. 1827 - 1834
(2007/10/03)
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- Benzophenone-Mediated Conjugate Additions of Aromatic Aldehydes to Quinones
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Benzophenone increases the efficiency of the photochemically mediated addition of aldehydes to quinones.
- Kraus, George A.,Liu, Peng
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p. 7723 - 7726
(2007/10/02)
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- Utilization of Basic Alumina in a One-Pot Synthesis of 1,4-Diketones, 1,4,7-Triketones, and Dihydrojasmone by Conjugate Addition of Nitroalkanes to Enones
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The one-pot synthesis of functionalized 1,4-diketones was achieved in good yields by conjugate addition of primary nitroalkanes to α,β-unsaturated carbonyl compounds on basic alumina without solvent, followed by in situ oxidation with 30percent aqueous hydrogen peroxide in methanol.The one-pot syntheses of 1,4,7-triketones and dihydrojasmone are also reported.
- Ballini, Roberto,Petrini, Marino,Marcantoni, Enrico,Rosini, Goffredo
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p. 231 - 233
(2007/10/02)
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- ACYLSILANE-MEDIATED NUCLEOPHILIC ACYLATION OF α,β-UNSATURATED CARBONYL DERIVATIVES
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A number of 1,4-diketones and of γ-keto esters can be prepared regiospecifically under mild conditions by employing a TBACN-catalysed Michael addition of acylsilanes to α,β-unsaturated carbonyl derivatives.
- degl'Innocenti, Alessandro,Ricci, Alfredo,Mordini, Alessandro,Reginato, Gianna,Colotta, Vittoria
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p. 645 - 648
(2007/10/02)
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- Selective catalyzed-rearrangement of terminal epoxides to methyl ketones
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Terminal epoxides of the type {A figure is presented} have been selectively converted into methyl ketones by various catalysts. Some lanthanide derivatives, MnI2, and Co2(CO)8 gave the best results. The rearrangement of internal epoxides into ketones is much slower, allowing specific transformation of terminal epoxides. The scope of the reaction and tentative mechanisms are discussed.
- Prandi,Namy,Menoret,Kagan
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p. 449 - 460
(2007/10/02)
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- REGIOSELECTIVE SYNTHETIC ROUTES TO 1,4-DICARBONYL COMPOUNDS AND SOME α-HYDROXY CARBONYL COMPOUNDS FROM 1,1-BIS(THIO)- AND BIS(SELENO)-ALLKYLLITHIUMS
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CuCl2/CuO was found to be a particularly valuable combination for the transformation of functionalized thio- and seleno-ketals to the corresponding aldehydes and ketones.
- Lucchetti, Jean,Krief, Alain
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p. 1153 - 1162
(2007/10/02)
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- ADDITION CONJUGUEE D'EQUIVALENTS D'ACYLES AUX CYCLOHEXEN-2 ONES ET A LA Δ1(9) OCTALONE-2 : SYNTHESE DE DICETONES 1-4.
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The synthesis of 3-acetylcyclohexanones 11, 12, 13 has been realized by conjugate addition of lithiated cyanohydrin ether 1a to 2-cyclohexanones 2, 3, 4 in THF-HMPA, even if 3-substituted. 3-benzoylcyclohexanones 14, 15, 16 are obtained from 1b and 2, 3,
- Seuron, Nadine,Wartski, Lya,Seyden-Penne, Jacqueline
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p. 2175 - 2178
(2007/10/02)
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- Copper 'ate' complexes of α-ethoxyvinyl-lithium: Reagents for coupling and 1,4 addition of a masked acyl anion
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Stoicheiometric and mixed organocuprate reagents have been prepared from α-ethoxyvinyl-lithium and undergo ready conjugate addition and coupling reactions.
- Boeckman Jr., Robert K.,Bruza, Kenneth J.,Baldwin,Lever Jr.
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p. 519 - 520
(2007/10/12)
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