- Henry reaction of fluorinated nitro compounds
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The Henry (nitroaldol) reaction of fluorinated nitro compounds with various aromatic aldehydes and a fluorinated aliphatic aldehyde to give β-fluoro-β-nitroalcohols which bearing a fluorinated quaternary carbon center was reported. The relative configuration of the major diastereoisomer of 2-fluoro-2-nitro-1-(4-nitrophenyl)-3-phenylpropanol (5bf) was determined by X-ray single crystal analysis.
- Hu, Huawei,Huang, Yangen,Guo, Yong
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- General method for the synthesis of isoxazoline N-oxides from aliphatic nitro compounds
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A method for the synthesis of isoxazolines N-oxides from primary aliphatic nitro compounds and olefins based on the 1,3-dipolar cycloaddition of intermediate 1-halo-substituted silyl nitronates, followed by halosilane elimination has been described. The n
- Kunetsky, Roman A.,Dilman, Alexander D.,Struchkova, Marina I.,Belyakov, Pavel A.,Tartakovsky, Vladimir A.,Ioffe, Sema L.
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- Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis
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Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.
- Cao, Haoying,Ma, Shanshan,Feng, Yanhong,Guo, Yawen,Jiao, Peng
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supporting information
p. 1780 - 1783
(2022/02/17)
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- Diethyl fluoronitromethylphosphonate: Synthesis and application in nucleophilic fluoroalkyl additions
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Diethyl fluoronitromethylphosphonate (3), a previously unknown compound, was synthesized by electrophilic fluorination of diethyl nitromethylphosphonate with Selectfluor. Base-induced decomposition of 3 was studied by NMR spectroscopy, which identified diethyl fluorophosphate and fluoronitromethane as the main decomposition products. C H acidities [pKa values in dimethyl sulfoxide (DMSO)] of 3, 1-fluoro-1-phenylsulfonylmethanephosphonate (1; McCarthy's reagent), tetraethyl fluoromethylenebisphosphonate (2), and some nonfluorinated phosphonates were computed, and a good correlation between calculated and experimental pKa values was found. The calculated C-H acidities increased in the sequence 2a,b-unsaturated carbonyl compounds, sulfones, and nitro compounds allowed access to variously modified diethyl 1-fluoro-1-nitrophosphonates.
- Opekar, Stanislav,Pohl, Radek,Beran, Pavel,Rulisek, Lubomir,Beier, Petr
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supporting information
p. 1453 - 1458
(2014/04/03)
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- Convenient fluorination of nitro and nitrile compounds with Selectfluor
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A variety of nitro and nitrile compounds were fluorinated in good yields by Selectfluor under mild conditions. For these transformations to be successful, it is crucial to select proper amounts of an appropriate base as a function of the properties of the substrate and also to use Selectfluor only as required.
- Peng, Weimin,Shreeve, Jean'ne M.
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p. 4905 - 4909
(2007/10/03)
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- Chemistry of Novel Compounds with Multifunctional Carbon Structure. 5. Molecular Design of Versatile Building Blocks for Aliphatic Monofluoro Molecules by Manipulation of Multifunctional Carbon Structure
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Three kinds of doubly functionalized monofluoromethylene fragments, 1-fluoro-1-nitro-1-(phenylsulfonyl)alkanes (10), 2-fluoro-2-(phenylsulfonyl)alkanoic esters (11), and 2-fluoro-2-nitroalkanoic esters (12), potentially versatile building blocks for the general synthesis of various aliphatic monofluoro molecules, were prepared from the corresponding difunctional compounds 1-3 by monoalkylation (R) and selective fluorinations.The interconversion or reductive removal of each functional group in 10-12 followed by the introduction of the second alkyl groups (R') at the fluorine-bearing carbon atom was examined.Compounds 12 proved to be useful and practical building blocks for conversions to the various monofluoroalkanes 20-26.
- Takeuchi, Yoshio,Nagata, Kazuhiro,Koizumi, Toru
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p. 5453 - 5459
(2007/10/02)
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- The First Versatile and Practical Building Blocks Equivalent to the Synthon of Monofluoromethylene Dicarbanion
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New monofluorinated synthons have been prepared.The use of α-fluoro-α-nitro carboxylic esters as versatile building blocks was demonstrated by their conversion to various monofluorinated compounds via fluoromethyl anion and fluoromethylene dianion equivalents.
- Takeuchi, Yoshio,Nagata, Kazuhiro,Koizumi, Toru
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p. 5061 - 5063
(2007/10/02)
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