Bis(iodozincio)methane as a synthetic tool
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概要
- 論文の詳細を見る
Bis(iodozincio)methane was prepared from diiodomethane and zinc in the presence of a catalytic amount of lead. The compound showed a high potential as an organic synthetic reagent. The reaction with carbonyl compounds proceeded to give methylenated products. The reagent also reacted with a couple of electrophiles sequentially. The function as Lewis acid is also unique. It coordinated with 1, 2-dicarbonyl compounds in face-to-face manner and assisted the stepwise nucleophilic attack on the carbon center of the reagent; the products are cis-1, 2-cyclopropanediols. A structural study was also examined.(Communicated by Hitosi NOZAKI, M. J. A., March 12, 2003)
- 日本学士院の論文
著者
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MATSUBARA Seijiro
Department of Material Chemistry, Kyoto University
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OSHIMA Koichiro
Department of Material Chemistry, Graduate School of Engineering, Kyoto University
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Matsubara Seijiro
Department Of Material Chemistry Faculty Of Enginnering Kyoto University
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Oshima Koichiro
Department Of Material Chemistry Graduate School Of Engineering Kyoto University
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Oshima Koichiro
Department Of Industrial Chemistry Faculty Of Engineering Kyoto University
関連論文
- Fullerene and Sulfur Compounds
- Copper-Catalyzed Arylation of Chlorosilanes with Grignard Reagents
- Palladium-catalyzed Mizoroki-Heck Reactions of 2-Methylene-1,3-dithiane 1-Oxide with Aryl Iodides
- Synthesis of β,γ-Unsaturated Ketones from Acid Chlorides through Carbon-Pentamethylcyclopentadienyl Bond Formation and Cleavage
- Synthesis of Prenylarenes and Related (Multisubstituted Allyl)arenes from Aryl Halides and Homoallyl Alcohols via Palladium-Catalyzed Retro-Allylation
- Selectivity in Organic Group Transfer in Reactions of Mixed Diorganomanganese(II) and Triorganomanganate(II) with 2-Cyclohexen-1-one or Cyclohexanecarbaldehyde
- Manganese-Catalyzed Silylmagnesiation of Acetylenes and 1,3-Dienes
- Manganese-catalyzed Phenylation of Acetylenic Compounds with a Phenyl Grignard Reagent
- Preparation of Deuterium Labelled Organophosphonium Salts (Wittig Salts) under Hydrothermal Condition Catalyzed by Molecular Sieves
- Vanadium-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents
- Trialkylmanganate Mediated Radical Addition of Triphenylgermane to Carbon-Carbon Multiple Bonds
- Ruthenium-catalyzed Isomerization of Alkenol into Alkanone in Water under Irradiation of Microwaves
- Radical Addition of α-Halo Ester to Homoallylic Gallium or Indium Species : Formation of Cyclopropane Derivatives
- Allylation of Carbonyl Compounds with Allylic Gallium Reagents
- Carbazole Synthesis by Platinum-catalyzed C-H Functionalizing Reaction Using Water as Reoxidizing Reagent
- Preparation of Organoytterbium Reagent from Ytterbium Trichloride and Organomagnesium
- Stereoselective Allylation of 3-Oxo Amides
- Preparation of Ester-group Substituted Allylic Zinc by Palladium-catalyzed Umpolung of γ-Acyloxy-α,β-unsaturated Ester by Bis(iodozincio)methane
- Nickel-catalyzed [4+2] Cycloaddition of Alkynes to Carbonylsalicylamides via Elimination of Isocyanates
- Ruthenium Catalyzed Deuterium Labelling of α-Carbon in Primary Alcohol and Primary/Secondary Amine in D_2O
- Palladium-Catalyzed H-D Exchange Reaction under Hydrothermal Condition
- S_N2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water
- Synthesis of Coordinatively Unsaturated Cobalt(II)-Alkyl Complexes Bearing Phosphorus-bridged [1.1]Ferrocenophanes
- Preparation and Reaction of Phenylsulfonyl-substituted Dizinciomethane
- Facile Preparation of Vicinal Allylsiloxy-and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
- Ytterbium Catalyzed Oxidation of Alcohols to Aldehydes and Ketones by Means of Iodosylbenzene
- Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes and 3-Silabicyclo[3.3.0]oct-1-enes
- Stereocontrolled Reduction of 2-Acyl-1,3-oxathiane Derivatives by Zn(BH_4)_2 and YCl_3-NaBH_4
- 2-Lithio-2-trimethylsilyl-1-silacyclopentane as a Synthetic Equivalent of 1-Lithio-1,4-butanediol
- Radical Addition of Polyhaloalkanes to 2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Radical Addition of Alkyl Halides to 2-Methylene-1,3-dithiane Monoxide as a Ketene Equivalent
- Extended Pummerer Reaction of Arylketene Dithioacetal Monoxides with Aromatic Compounds by Means Trifluoromethanesulfonic Anhydride
- Triethylborane-Induced Radical Reaction of Alkynylgallium with α-Halo Carbonyl Compounds
- Triethylborane Induced Radical Reaction of Gallium Enolates with α-Halo Esters
- Tributylmanganate(II)-Mediated Cyclization of Enynes
- Sequential Introduction of Carbon Nucleophiles onto Silicon Atoms Using Methyl as a Leaving Group
- Bis(iodozincio)methane as a synthetic tool
- Samarium Diiodide-Mediated Reaction of Organic Halides with Carbonyl Compounds
- A Preparation of β-Oxoester Enolate Equivalents from SmI_2 and α-Bromoalkanoates
- Preparation of Dialkoxyborylbis(bromozincio)methane and Its Reaction with Electrophiles
- Preparation of Zinc-Homoenolate from α-Sulfonyloxy Ketone and Bis(iodozincio)methane
- Wittig Type Methylenation of Ketones with Bis(iodozincio)methane and Ionic Liquid
- The Rate Enhancement Effect of Protodesilylation of Arylsilane Derivatives
- Iron(II) Chloride-mediated Addition of Dialkylmagnesium to Carbonyl Compounds
- Fabrication of Nano-structure by Diels-Alder Reaction
- Synthesis of Pyrimidines via Base-induced Condensation of α-Chloro Oxime Derivatives
- Cobalt-catalyzed Cross-coupling Reactions of Aryl Bromides with Alkyl Grignard Reagents
- Regio- and Stereoselective Additions of Diphenyldithiophosphinic Acid to N-(1-Alkynyl)amides and 1-Alkynyl Sulfides
- Silylcupration and Copper-Catalyzed Carbomagnesiation of Ynamides : Application to Aza-Claisen Rearrangement
- Regio- and Stereoselective Hydrothiolation Reactions of Ynamides with Diphenyldithiophosphinic Acid : Straightforward Synthesis of Ketene N,S-Acetal Derivatives
- Transformations of N-Allyl-N-(phenylethynyl)arenesulfonamides into 2,2-Disubstituted 4-Pentenenitriles through Aza-Claisen Rearrangement that Follows Carbomagnesiation
- Cobalt-Catalyzed Allylzincations of Internal Alkynes
- Radical Cyclization of Allyl 2-Iodophenyl Ether,N,N-Diallyl-2-iodoaniline, and 2-Iodoethanal Acetal by Means of Trialkylmanganate(II)
- Rhodium-Catalyzed Reaction of 1-Alkynylphosphines with Water Yielding (E)-1-Alkenylphosphine Oxides
- Atom-transfer Radical Addition of α-Iodo Esters to 1-Alkynyl Sulfides
- Palladium-Catalyzed 1-Methylene-2-propenylation Reactions of Aryl Bromides with 3,4-Alkadien-1-ols via Carbon-Carbon Bond Cleavage for the Synthesis of 2-Aryl-1,3-butadiene Derivatives
- Efficient Aerobic Oxidation of Phosphines, Phosphites, and Sulfides by Using Trialkylborane
- Copper-Catalyzed Allylation of Alkyl Halides with Allylic Grignard Reagents
- Development of Radical Reactions with Zirconocene Complexes as Electron Transfer Reagents
- Nickel-catalyzed Carbometalation Reactions of [2-(1-Propynyl)phenyl]methanol with 1-Alkenylmagnesium Reagents
- Cobalt-catalyzed Cross-coupling Reaction of Chloropyridines with Grignard Reagents
- Radical Addition of 2-Iodoalkanamide or 2-Iodoalkanoic Acid to Alkenes with a Water-Soluble Radical Initiator Initiator in Aqueous Media: Facile Synthesis of γ-Lactones
- Reduction of Organic Halides with Tri-2-furylgermane: Stoichiometric and Catalytic Reduction
- Radical Cyclization of N-Allyl-2-halo Amide in Water
- Radical Cyclization Reaction Using a Combination of Phosphinic Acid and a Base in Aqueous Ethanol
- Three-step α-Acylation of (E)-Cinnamate Esters with Inversion of Stereochemistry through Formation and Cleavage of Carbon-Pentamethylcyclopentadienyl Bonds
- Metal-Mediated Retro-Allylation of Homoallyl Alcohols for Highly Selective Organic Synthesis
- Cobalt-Catalyzed Allylic Substitution Reaction of Allylic Ethers with Phenyl and Trimethylsilylmethyl Grignard Reagents
- Highly Selective Synthetic Reactions by the Combined Use of Organometallic Reagents and Radical Species
- Triethylborane-Induced Radical Reactions in Ionic Liquids
- Stereoselective Reduction of α,β-Epoxy Ketones into erythro-α,β-Epoxy Alcohols with Sodium Borohydride in the Presence of Calcium Chloride
- Manganese (II) Chloride-Catalyzed Alkylmagnesation of 2-Alkynylphenol
- Reaction of 1, 3-Dihalopropene with Trialkylmanganate
- Nickel-catalyzed Decarbonylative Cycloaddition of Phthalic Anhydrides with 1,3-Dienes
- Nickel-catalyzed Cycloadditions of Benzoxazinones with Alkynes : Synthesis of Quinolines and Quinolones
- Wittig Like Methylenation of Aldehydes in a Microflow System: Selective Methylenation by Differential of Plural Reactions
- Methylenation of Esters with Bis(iodozincio)methane-TiCl_2-TMEDA System
- A Facile Synthesis of 1,1-Disilylethenes via Me_3MgLi-Induced Monomethylation of Dibromodisilylmethanes
- Reaction of Trialkyl(dibromomethyl)silanes or 1,2-Bis(dibromomethyl)benzene with Triorganomanganates. A Facile and Selective Synthesis of Alkenylsilanes and 1,2-Diaryl-1,2-dihydrobenzocyclobutenes
- Radical Reaction by a Combination of Phosphinic Acid and a Base in Aqueous Media
- Nickel-catalyzed [3+2] Cycloaddition of α,β-Unsaturated Ketones with Vinyl Oxiranes
- Bis(cyclopentadienyldicarbonyliron) as a Convenient Carbon Monoxide Source in Palladium-catalyzed Carbonylative Coupling of Aryl Iodides with Amines, Alcohols, and Thiols
- Nickel-catalyzed Cycloaddition of Aromatic (O-Benzyl)ketoximes with Alkynes to Produce Isoquinoline and Isoquinoline N-Oxide Derivatives
- Nickel-catalyzed Heteroannulation of o-Haloanilines with Alkynes
- Nickel-catalyzed Decarboxylative Polymerization of 6-Alkynylisatoic Anhydride
- Rapid Preparation of Cycloheptane Ring from 1,2-Diketone and Bis(iodozincio)methane via Oxy-Cope Rearrangement Using Microflow System
- Triethylborane-induced hydrodehalogenation of organic halides by tin hydrides.
- Palladium Catalyzed Reaction of Silacyclobutanes with Acetylenes.
- The Reduction of gem-Dibromocyclopropanes by Means of Chromium(II) Acetate or Potassium Pentacyanocobaltate
- Cross-coupling reaction between enol phosphates and organoaluminium compounds in the presence of palladium(0) catalyst.
- Isomerization of allylic alcohols catalyzed by vanadium or molybdenum complexes.
- Reformatsky type reaction with new aluminium reagents containing Al-Sn or Al-Pb linkage.
- New methods for the synthesis of 3(2H)-furanones and 2(5H)-furanones.
- Palladium catalyzed hydrostannylation and hydrogermylation of acetylenes.
- Hydrostannation and hydrogermylation of allenes.
- Measurements of double differential neutron emission cross sections for fusion reactor candidate elements.
- Intramolecular cyclization of nerol and the related attack of (Z)-allylic alcohol moiety on the terminal olefin linkage as induced by TiCl4-PhNHMe complex. Synthesis of nezukone.
- Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.
- Carbocyclic ring formation by the intramolecular reaction between enol silyl ether and allylic acetate moieties.