Reactions of alkyl diphenylphosphinates and related thio esters with some nucleophiles. SN2 (S) reaction and Wittig type rearrangement.

スポンサーリンク

概要

• 論文の詳細を見る

• Reactions of alkyl diphenylphosphinates Ph<SUB>2</SUB>P(=X)YCHR<SUP>1</SUP>R<SUP>2</SUP> (X, Y=O,S) with organolithiums and Grignard reagents afforded different types of products depending on the combination of X and Y. When Y=O, the reagents (R<SUP>3</SUP>M) mainly attacked the phosphorus atom to give Ph<SUB>2</SUB>P(=X)R<SUP>3</SUP> and R<SUP>1</SUP>R<SUP>2</SUP>XCHO<SUP>−</SUP> irrespective of X, while, when X=Y=S, the reaction occurred exclusively at the ester sulfur atom, <I>S</I><SUB>N</SUB>2(S), to give R<SUP>3</SUP>SCHR<SUP>1</SUP>R<SUP>2</SUP> and [Ph<SUB>2</SUB>PS]<SUP>−</SUP>. When the X=O and Y=S, a Wittig type rearrangement of a carbanion [Ph<SUB>2</SUB>P(=O)SCR<SUP>1</SUP>R<SUP>2</SUP>]<SUP>−</SUP> was observed along with attacks on the phosphorus (major) and the sulfur (minor) atoms. Reactions with some other nucleophiles (hydride, amide and alkoxide ions) are also described.

• 公益社団法人 日本化学会の論文

著者

• Akiba Kin-ya

  Department Of Chemistry Faculty Of Science Hiroshima University

• Inamoto Naoki

  Department Of Chemistry Graduate School Of Science The University Of Tokyo

• Okazaki Renji

  Department Of Chemical And Biological Sciences Faculty Of Science Japan Women's University

• Goda Koshiro

  Department of Chemistry, Faculty of Science, The University of Tokyo

関連論文

• Synthesis of Unsymmetrically Substituted Antimony(V) Tetraphenylporphyrins
• Monomeric 10-Sb-5 Pentacoordinate Organoantimony Monohalides and Their Permutational Behavior
• Synthesis, Structure, and Reactions of 10-Sn-5 Organotin Ate Complexes
• Synthesis, Structure, and Reactions of a 10-Sb-4 Type Antimony Ate Complex
• Synthesis, Structure, and Some Reactions of (2,4,6-Tri-t-butyl)thiobenzaldehyde, the First Stable Aromatic Thioaldehyde
• Reaction of a Stable Silylene-Isocyanide Complex with Nitrile Oxides:A New Approach to the Generation of a Silanone
• Intramolecular Dehydration of β-Hydroxyalkylphosphonic Acid Monoesters. A Novel Type of Olefin Formation
• The Chemistry of Germanium-Containing Heavy ketones
• Formantion and Reactions of the First Diarylgermanone Stable in Solution
• Thermal Retrocycloaddition of Overcrowded Germirenes. A New Method for the Generation of Gerdmylenes
• Reaction of Stable Sulfenic and Selenenic Acids Containing a Bowl-type Steric Protection Group with a Phosphine. Elucidation of the Mechanism of Reduction of Sulfenic and Selenenic Acids
• Structural Elucidation of 1,3-Phenylenebis(methylene)-Bridged Calix[6]arenes with Four Uncapped Hydroxy Groups
• Different Aggregating Properties of Two Conformationally Frozen Isomers of a Water-Soluble Bridged Calix[6]arene
• The Olefin Synthesis from β-Hydroxyalkylphosphonates Induced by Fluorides or Relatively Weak Bases
• Cycloaddition and Oxidation Reactions of a Stable Thioaldehyde, (2,4,6-Tri-t-butyl)thiobenzaldehyde
• Synthesis, Stereochemistry, and Thermolysis of β-Aminoalkylboranes
• Thermolysis of β-Siloxyalkylboranes: Formation of Alkenes and/or Silyl Enol Ethers
• Reactions of (2,4,6-Tri-t-butyl) thiobenzaldehyde with Diazo Compounds. Synthesis and Reactions of Sterically Congested Thiiranes
• Structure and Thermolysis of a 1,4,2-Oxatellurazole, a Novel Tellurium Containing Heterocycle
• Reaction of 2,4,6-Tri-t-butylselenobenzaldehyde with Sterically Crowded Diazo Compounds. Formation of Seleniranes
• Synthesis of Δ^3 -1,3,4 -Telluradiazolines, a Novel Tellurium - Containing Heterocycle
• The Phospha-Cope Rearrangement of 3-Phospha-1,5-hexadiene Derivatives Bearing a Hydroxyl Group
• Synthesis and Unusual Photochemical Reaction of Highly Congested 2,4,6-Tri-t-butylstyrene Episulfides
• Structure of Azabismocines, Hexacoordinate Pentavalent Organobismuth Compounds
• Synthesis and Reactions of the First Stable 1-Germaallene
• The First Spectroscopic Observation of an Equilibrium between a Digermene and Germylenes and Experimental Determination of a Bond Dissociation Energy of a Ge-Ge Double Bond
• Oxidation and Thermolysis of a Stable Germaketenedithioacetal Derivative
• Synthesis and X-Ray Structures of Arsenic(V) Porphyrins with Symmetric Diaxial Ligands of Me_2 and F_2
• A New Preparative Route to Phosphaethynes from Dichlorophosphaethenes by Lithiation, Photoisomerization, and Re-lithiation Involving Migration
• Control Factors of Two Reaction Modes of Pentacoordinate 1,2-Oxasiletanides, the Peterson Reaction and Homo-Brook Rearrangement
• ^Sb Mossbauer Spectra of Hexafluorocumyl Alcohol Complexes of Sb(V), and of Sb(III) with Negative Quadrupole Coupling Contants
• Synthesis and Pseudorotational Barriers of Hypervalent Antimony Compounds Bearing Antimony-Group 6 Transition Metal Bonds
• Characterization of Enantiomeric Paris of Optically Active 10-P-5 Phosphoranes with Asymmetry Only at Phosphorus^
• Micropolarity around a Zwitterionic Solvatochrome Covalently Fixed in the Cavity of Bowl-Shaped Cyclophanes
• Synthesis of Novel Water-soluble Molecular Bowls and Their Unique Complexing Behavior with 1-Anilinonaphthalene-8-sulfonate
• Isolation of Two Conformationally Frozen Isomers of a Bridged Calix[6]arene
• Synthesis and Thermolysis of Tetracoordinate 1,2-Oxaphosphetanes Stabilized by Steric Protection
• Synthesis of Optically Active Phosphorus Compounds via Metal Phosphinites Generated by Reaction of Optically Active Selenophosphinates with Phenyllithium
• Novel Intermolecular Cyclization Reaction Involving a Thionitroso Group : Formation of a 3,3a-Dihydro-2,1-benzisothiazole from an o-Alkylthionitrosoarene
• Synthesis of Kinetically Stabilized Silaneselone and Silanetellone
• The First Stable Aromatic S-Nitrosothiol: Synthesis, Structure and Reactivity
• The First Chemical Trapping of Stibinidene,a Monovalent Antimony Compound
• Generation and Reactions of an Overcrowded Diaryldilithiosilane
• Synthesis, Structure, and Reactivity of Kinetically Stabilized Low-coordinated Organolead Compounds
• Synthesis of the First Stable Selenadistibirane and Its Molecular Structure
• An Unexpected Elimination of Cyclopentadienide Anion in the Reaction of Silacyclohexadienes with a Bulky Aryllithium
• Biscyanines Linked by a 1,8-Naphthylene Skeleton : Models of Polymethine Dye Aggregates
• Linear and Stack Oligostreptocyanines. Effects of Relative Orientation of Chromophores on Redox Potentials of Dye Aggregates
• Syntheses and Crystal Structures of Novel Antimony-Containing Cyclic Polysulfides^1
• Thermal Dissociation of Disilenes into Silylenes
• A New Method for the Synthesis of Stannylenes : Exhaustive Desulfurization of Tetrathiastannolanes
• Unusual Oxidation Reaction of an Overcrowded Thiagermacyclohexene Derivative
• Deprotonation of Aryl Methanedithioate by Lithium Amides : Formation of Lithium Arylthio(thioxo)methanide Having Unique Reactivity
• Synthesis and Reactions of the First Lead-Sulfur Double-Bond Compounds, Plumbanethiones
• Synthesis and Structure of a Novel Cyclic Polysulfide, 2,4,6-Tris[bis(trimethylsilyl)methyl]phenyloctathionane
• 1,2,3,4,5,6,7,8-Octathionane, a Novel Cyclic Polysulfide. Synthesis and Crystal Structure
• Fragmentations of 1, 2-Diethoxyethane by Electron Impact
• Highly Z-Selective Synthesis of Disubstituted α,β-Unsaturated Cyanides and Amides Using 10-P-5 Wittig Type Reagents
• Metal Phosphinylides and Phosphinothioylides. II. Effects of Metals on the Reactions of [Ph2PX]M with Benzaldehyde and p-Benzoquinone
• Chemistry of Nitrosoimines. VI. Attempted Syntheses of Some Resonance Stabilized Nitrosoimines and Their UV Spectra
• A Grignard-type addition of allyl unit to aldehydes by using bismuth and bismuth salt.
• Chemistry of N-thiosulfinylanilines. V. Reactions of N-thiosulfinylanilines with nucleophilic reagents.
• Chemistry of N-thiosulfinylanilines. III. Thiosulfinylamine-5H-1,2,3-dithiazole equilibrium as studied by NMR spectroscopy.
• Chemistry of N-thiosulfinylanilines. II. Thermolysis and photolysis of N-thiosulfinylanilines.
• Oxidation of 4-alkyl-1-hydroxyimino-2,4,6-tri-t-butyl-2,5-cyclohexadienes. Formation of 4-alkyl-2,6-di-t-butylnitrobenzenes via iminoxyl radical.
• Reaction of 2,4,6-tri-t-butylnitrobenzene with alkyl Grignard reagents.
• Chemistry of N-thiosulfinylanilines. IV. Reactions of N-thiosulfinylanilines with electrophilic reagents.
• Chemistry of N-thiosulfinylanilines. I. Reactions of sterically hindered anilines with sulfur chlorides. Preparation of N-thiosulfinylanilines.
• Reaction of Dichlorotriphenylphosphorane with Bis(trimethylsilyl) Peroxide. A New Method for the Formation of Electrophilic Chlorine Source.
• Synthesis and reactions of o-naphthothioquinone methides.
• Revised structure of 2-cyclohexyl-3,4-diphenyl-1,2-oxaphosphetane 2-oxide.
• Synthesis and reactions of o-benzothioquinonemethides.
• Reactions of ketone hydrazones and .BETA.-keto enamines with disulfur dichloride. New synthesis of thioketones and 5H-1,2,3-dithiazoles.
• Cycloaddition reactions of thioacylketene thioacetals and N-thioacyldithioimidocarbonates.
• Phosphinidenes and Related Intermediates. III. Reactions of Phosphinylidenes and Phosphinothioylidenes with Conjugated Dienes
• Photolytic and Thermal Decompositions of 5-Substituted 1,2,3,4-Thiatriazoles in the Presence of Olefins. Reactions of Sulfur Atoms
• Synthesis and properties of o-thioquinone methides having ketene aminal, ketene acetal, ketene monothioacetal, or ketene dithioacetal group.
• Reactions of alkyl diphenylphosphinates and related thio esters with some nucleophiles. SN2 (S) reaction and Wittig type rearrangement.
• Oxidation of Diphosphine Dioxides, Disulfides and Phosphinothioite and Photolysis of Diphosphine Disulfides. Formation of Phosphinic and Phosphinothioic Anhydrides
• Reactions of thioacylketene thioacetals and o-thioquinone methides with enamines.
• A mechanistic study on the reaction of iminothiadiazolines with activated acetylenes: Competitive pathway through hypervalent sulfurane and zwitterion.
• Chemistry of nitrosoimines. XIV. Photolysis of 5-nitrosoimino-4-phenyl-3-phenylimino-1,2,4-thiadiazolidine.
• Reactions of Nitrones with Free Radicals. II. Formation of Nitroxides
• Fluoride ion-induced Horner-Emmons reaction of .ALPHA.-silylalkylphosphonic derivatives with carbonyl compounds.
• Chemistry of Nitrosoimines. X. Reactions of 3-Substituted 2-Nitrosoimino-2,3,-dihydrobenzothiazoles with Aryl and t-Butyl Grignard Reagents
• Reactions of Diphenylphosphinothioyl Isothiocyanate and Related Compounds with Some Nucleophiles and Carbodiimides
• Belousov-Zhabotinskii reaction with 2,3-diones.
• Alkylation of the sulfur- and nitrogen-containing compounds analogous to thiazoline systems.
• Preparation of tetraalkyl 2,2'-phthaloylbis(1,2-dihydro-1-isoquinolylphosphonate)s and their reactions with base.
• Reactions of aldonitrones with phenylphosphonothioic dichloride and related compounds. Formation of 2-arylbenzothiazoles from .ALPHA.,N-diarylnitrones.
• Alkylation of benzothiazolines and the Stevens rearrangement of the resulting 2,3,3-trisubstituted benzothiazolinium salts.
• Preparation and hydrolysis of some sterically protected 1-aza-3-phosphaallenes.
• A convenient method for the regioselective synthesis of 4-alkyl(aryl)pyridines using pyridinium salts.
• Phosphinidenes and related intermediates. IV. Reactions of phosphinothioylidenes with cis- and trans-stilbene oxides.
• Metal Phosphinylides and Phosphinothioylides. IV. Reactions with Tetrahydrofuran
• Elucidation of the origin of substituent effects. Theoretical investigation of field effect in aliphatic systems by ab initio molecular orbital calculation using simple models.
• Equilibrium and 31P chemical shifts of the adducts of trialkylphosphines and isothiocyanates, and reactions of triethylphosphine and benzoyl isothiocyanate.
• Reaction of Alkylidenephosphoranes with Nitrosyl Chloride and Decomposition of α-Hydroxyiminophosphonium Chlorides Formed
• Chemistry of Nitrosoimines. XII. Reactions of 3-Substituted 2-Nitrosoimino-2,3-dihydrobenzothiazoles with Alkyl Grignard Reagents
• Chemistry of Nitrosoimines. XI. Reactions of 3-Substituted 2-Nitrosoimino-2,3-dihydrobenzothiazoles with Benzyl and Allylic Grignard Reagents

もっと見る 閉じる

スポンサーリンク