Reaction of coordinated phosphines. IV. Mechanism of carbon-phosphorus bond cleavage in triarylphosphines and trialkylphosphines by palladium(II) acetate.
スポンサーリンク
概要
- 論文の詳細を見る
Reaction of triphenylphosphine with an equimolar amount of Pd(OAc)<SUB>2</SUB> in acetic acid at room temperature in the presence of styrene gave <I>trans</I>-stilbene(94%), H<SUB>3</SUB>PO<SUB>4</SUB>(0.8%), PhP(O)(OH)<SUB>2</SUB>(40%), Ph<SUB>2</SUB>P(O)(OH)(19%), and Ph<SUB>3</SUB>P=O(35%). Reactions of tributyl- and trioctylphosphine with Pd(OAc)<SUB>2</SUB> in acetic acid at 90 °C yielded butene(20%) and octene(1-; 22%, 2-; 17%), respectively, as main products. The phenylation of some olefins with triphenylphosphine in acetic acid-<I>d</I>, as well as other features of the reaction lead to the conclusion that nucleophilic attack on coordinated phosphorus atom is the most probable pathway for the formation of the phenylation agent (phenylpalladium species) in the reaction system among the others, <I>ortho</I>-metallation and oxidative addition.
- 公益社団法人 日本化学会の論文
著者
-
MATSUDA Tsutomu
Department of Chemistry and Chemical Engineering, Faculty of Technology, Kanazawa University
-
Kikukawa Kiyoshi
Department Of Biological And Environmental Chemistry Kinki University
-
Takagi Makoto
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
関連論文
- Deformation Behavior of Pt-based Metallic Glass at Elevated Temperatures
- Crystallization of Zr_Al_Ni_5Cu_ Bulk Metallic Glass Composites Containing ZrC Particles
- Microstructure of Superplastic Zr_Al_Ni_Cu_ Metallic Glass
- Photoisomerizable DNA Ligands. Spectral and Electrochemical Properties and Base-Pair Selectivity of Binding of Bis[2-(1-alkylpyridinium-4-yl)vinyl]benzen Dyes
- Threading Intercalators as a New DNA Structural Probe
- NOVEL LIQUID ANION-EXCHANGE EXTRACTANT. ETHYLENEBIS(TRIOCTYLPHOSPHONIUM) SALT, BEARING TWO CATION CENTERS ADJACENTLY IN A MOLECULE
- Direct Detection of Single Nucleotide Polymorphism (SNP) with Genomic DNA by the Ferrocenylnaphthalene Diimide-based Electrochemical Hybridization Assay (FND-EHA)
- Electrochemical Detection of Base Pair Mutation
- フェロセン化ナフタレンジイミド誘導体の電気化学とそのヘアピンDNA修飾電極での挙動
- Enhanced Electron Transfer from Glucose Oxidase to DNA-Immobilized Electrode Aided by Ferrocenyl Naphthalene Diimide, a Threading Intercalator
- Enhanced Quantum Yield in Porphyrin Solar Cell with Redox Chain for Electron Transfer
- Formation Condition of Fiberform Nanostructured Tungsten by Helium Plasma Exposure
- Observation of High Dose H^+ Implanted Damaged Layer
- Lipophilic Peptide as Novel Sensory Material for Chiral Amine Recognition
- Lipophilic Peptide as Novel Building Material of Molecular Sensor
- Selective Colorimetry of Sodium Ion in Anionic Micellar Solution Containing Dibenzo-16-crown-5 Chromoionophore
- Fluorescence Detection of DNA Using a Novel Peroxidase Substrate, 4-(4-Hydroxyphenylcarbamoyl)butanoic Acid
- Sodium Ion Photometry in Aqueous Media by a Dibenzo-16-crown-5 Chromoionophore
- A Novel Method for Determining Peroxidase Activities Using ρ-Acetamidophenol Analogs
- A Cyclic Sugar Unit Interacts More Strongly with DNA Than Do Open-Chain Polyol Counterparts in Sugar-Linked Synthetic DNA Intercalators
- Preparation of Ferrocyanide-Imprinted Pyridine-Carrying Microspheres by Surface Imprinting Polymerization
- An Enantioselective Polymer Prepared by the Surface Molecular-Imprinting Technique
- NOVEL METAL ION-IMPRINTED RESINS PREPARED BY SURFACE TEMPLATE POLYMERIZATION WITH W/O EMULSION
- Template-Dependent Selectivity in Metal Adsorption on Phosphoric Diester-Carrying Resins Prepared by Surface Template Polymerization Technique
- TEM and HRTEM Observations of Microstructural Change of Silicon Single Crystal Scratched under Very Small Loading Forces by AFM
- Preparation of an Organic Acid-imprinted Resin by a Surface Imprinting Method
- Analysis of the Complex of Oligonucleotide Duplexes with Ligands by MALDI-TOF Mass Spectroscopy
- Condensed-Phosphate Imprinted Resins Prepared by a Surface Template Polymerization Method
- Photo - induced DNA Cleavage by Water - soluble Cationic Fullerene Derivatives
- Study of the DNA Interaction with Water - soluble Cationic Fullerene Derivatives
- DNA - Controlled Photosomerization of Bis(2 - (1 - methyl - pyridinium - 4 - yl)vinyl) benzene
- Liver metastasis of pancreatic cancer managed by intra-arterial infusion chemotherapy combined with degradable starch microspheres
- Gas Phase Basicities of α-Trimethylsilylstyrenes. Intrinsic Effect of α-Trimethylsilyl Group on the Stability of Carbenium Ions
- Preparation and Characterization of Polymer Microspheres Which Have Specific Binding Ability for Saccharide Molecules
- Preparation and Sugar Binding Property of Microspheres Having Surface-anchored Phenylboronic Acid Groups
- Development of Divertor Plasma Simulators with High Heat Flux Plasmas and its Application to Nuclear Fusion Study : A Review
- Surface Imprinting. Characterization of a Latex Resin and the Origin of the Imprinting Effect
- Gas-Phase Lithium Cation Basicities of Acetophenones : A Linear Relationship between Lithium Cation and Proton Basicities
- Adsorption of Metal Ions to Surface-Template Resins Prepared with Amphiphilic Styrene Monomers Bearing Amino Carboxylic Acid
- Selective Adsorption of Metal Ions to Surface-Template Resins Prepared by Emulsion Polymerization Using 10-(p-Vinylphenyl)decanoic Acid
- Light-Induced DNA Cleavage by Bis-9-acridinyl Viologen Derivative
- Hydrolysis of Nucleotides Using Actinoid Metal Ion
- CROWN ETHER-BASED EXTRACTION PHOTOMETRIC REAGENTS FOR CALCIUM
- Mg^-Selective Electrode Comprising Double-Helical DNA as Receptive Entity
- Ferrocyanide-Templated Resins Prepared by Surface Template Polymerization
- Characterization of Organic Compounds Eluted from Coal under Water Digestion〔含 討論〕
- EXTRACTION RATE-CONTROLLED SEPARATION OF METAL IONS
- CHROMOGENIC CROWN ETHER REAGENT SELECTIVE TO SODIUM
- High Hydrostatic Pressure Consolidation of Amorphous Ti-37.5 at%Si Powder Prepared by Mechanical Alloying and Mechanical Properties of the Compact
- Metallo-Regulation of DNA Triple Helix Formation through Cooperative Dimerization of Two Oligonucleotides
- Calix[n]arenes Provided with Thiols for Modified Electrode Applications;Ring-size Dependent Voltammetric Behavior toward Ferrocene Derivatives
- DNA Intercalators Bearing Metal Chelating Moiety. Ternary Complexes of Polyamine Containing Anthraquinone Derivative-DNA-Cu(II) and Its DNA Cleavage Activity
- Fries rearrangement in calixarene esters. A new entry for the synthesis of p-substituted calixarenes.
- Thermionic Energy Converter System Using Heat Flux in Divertor Region
- Catalytic Behavior of Rhodium(I) Complexes in Hydrogermylation and Hydrosilylation of Phenylacetylene.
- The Reaction of Open-chain Unconjugated Dienes with Palladium Acetate. Dependence of the Products on Disposition of the Two Double Bonds
- "pKa" of calixarenes and analogs in nonaqueous solvents.
- Synthesis of azobenzo-crown ethers and their complexation behavior with metal ions.
- Solvent extraction of palladium (II) and platinum (IV) with N, N-dioctylsuccinamic acid from aqueous chloride media.
- New syntheses and physical properties of p-alkylcalix(n)arenes.
- Syntheses of Organic Phosphates. II. 3-Hydroxy-2-pyridylmethyl, 6-Methyl-2-pyridylmethyl, 3-Pyridyl and 8-Quinolyl Phosphate
- The reductive acylation of organic disulfides with aldehydes under photochemical and radical conditions.
- New applications of crown ethers. II. Synthesis of 4'-formylbenzocrown ethers.
- New application of crown ethers. III. Synthesis of 4'-hydroxybenzocrown ethers and their bis(benzocrown ether)s linked by poly(oxyethylene) chain.
- Reaction of diazonium salts with transition metals. II. Palladium-catalyzed arylation of ethylene with arenediazonium salts.
- Reaction of coordinated phosphines. IV. Mechanism of carbon-phosphorus bond cleavage in triarylphosphines and trialkylphosphines by palladium(II) acetate.
- Reaction of coordinated phosphines. III. Reaction of phenyl compounds of typical groups V and VI elements with palladium(II) salts in the presence of olefinic compounds.
- Preparation and the properties of .PI.-allylic palladium(II) complexes of amino acid.
- New application of crown ether. V. The effect of crown ethers on the acid-base interaction between 2,4,4',6-tetranitrodiphenylamine and primary amines in benzene.
- New applications of crown ethers. IX. Crystal structure of KSCN complex of N-heptylmonoaza-18-crown-6, and conformational features of the pivot nitrogen.
- The solvent extraction of alkali and alkaline earth metal ions with nonionic and ionic surfactants having poly(oxyethylene) chain.
- Synthesis of crown ether dyes.
- Synthesis of 4′-Vinylbenzo-15-crown-5 from Benzo-15-crown-5
- The Reaction of Propargyl Compounds with Carbon Monoxide and Water in the Presence of Iron Carbonyl Catalyst
- Reaction of coordinated phosphines. V. Aryl and alkyl transfer from tertiary phosphine to transition metal.
- New applications of crown ethers. X. 13CNMR relaxation times study of cation-binding behavior of monoazacrown ethers and bis(monoazacrown ether)s.
- Photochemical reductive acylation and oxidative acyl activation on phenazine and related nitrogen heterocycles.
- Benzo-15-crown-5-aluminium chloride complexes of unusual stability.
- Palladium-catalyzed reaction of 4'-iodobenzocrown ethers with acetylenes. Convenient synthesis of alkyl-substituted benzocrown ethers and bis(benzocrown ether)s via alkynl-substituted benzocrown ethers.
- Effect of Crown Ether in the Reduction of Ketones with Sodium Borohydride in Aromatic Solvent
- Mono S-acylated 1,8-naphthalenedithiol. Isolation and characterization of tetrahedral intermediate in the intramolecular acyl transfer reaction.
- Generation of olefin metathesis catalysts from W(CO)6 and group IVa metal halides under photochemical conditions.
- The effect of crown ethers on the reaction of alkali metal trichloroacetate with cyclohexene under decarboxylative conditions.
- The solvent extraction of alkaline earth metal ions with nonionic surfactants.
- (2-Pyridylmethoxy)calixarenes: New versatile ionophores for metal extraction.