Selenocyanatodethallation in Organothallium(III) Compounds

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概要

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• Substitution of thallium moiety in organothallium(III) compounds by selenocyanate is reported. Arylthallium (III) compounds react with KSeCN and CuSO<SUB>4</SUB>·5H<SUB>2</SUB>O or with Cu(SeCN)<SUB>2</SUB> in dioxane to give aryl selenocyanates in good yields. Alkoxythallates of styrene react smoothly with KSeCN in methanol to afford 1-alkoxy-1-phenyl-2-selenocyanatoethanes almost quantitatively. The oxyselenocyanation of terminal oleflns is conducted by the <I>in situ</I> oxythallation of olefins, followed by the reaction with KSeCN.

• 公益社団法人 日本化学会の論文

著者

• Toshimitsu Akio

  Institute For Chemical Research Kyoto University

• Okano Masaya

  Institute for Chemical Research, Kyoto University

• Uemura Sakae

  Institute for Chemical Research, Kyoto University

• Ichikawa Katsuhiko

  Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University

関連論文

• Stereochemistry of the Intramolecular Substitution of Phnylselenonyl Group by Nitrogen Atom in Amide. Inversion of Configuration
• Nucleophilic Addition of a Divalent Silicon Species Bearing the 8-Dimethylamino-1-naphthyl Group to Diphenylacetylenes to Form the 1-Amino-1-silaphenalene Skeleton
• Trimerization of a Divalent Silicon Species Bearing the 8-Dimethylamino-1-naphthyl Group Accompanied by the Migration of Methyl and Dimethylamino Groups
• Wurtz - type Coupling Reaction of Pseudo - pentacoordinate Halodisilanes Using Magnesium : Enhanced Reactivity of the Silicon - Halogen Bond by Intramolecular Amine - Coordination to Silicon
• Intramolecular Cyclization Reaction via a Sterically Protected Episelenonium Ion Intermediate
• Enhanced Leaving Ability of Methoxy Group and Retarded Deprotonation on the Carbon Atom Linked to the 1-Position of 8-Phosphino- or 8-Amino-naphthalene
• Asymmetric Carbon-Carbon Bond Formations by the Reaction of "Chiral Episulfonium Ions" with Enol Silyl Ethers
• The formylation of an aromatic nucleus by the use of 2-ethoxy-1,3-dithiolane.
• The reactions of the 1,2-ethanediylbis(trithiocarbonic acid) dianion with several electrophilic reagents.
• Syntheses of aryl glyoxylate. I. The reaction of alkyl dichloro(alkoxy)acetates with aromatics in the presence of Lewis acid.
• The reactions of olefins with chloromethoxymethane or dimethoxymethane in nitriles.
• Synthesis and lithiation of 2-alkylthio- and 2-arylthio-1,3-dithiolanes.
• Selenium and tellurium tetrachlorides as reagents for the conversion of alcohols to alkyl chlorides and tellurium tetrachloride as a Lewis acid catalyst for aromatic alkylation.
• Chlorination of acetylenes with sulfuryl chloride.
• The formation of vinyl sulfides by the cleavage of the carbon-sulfur bond in dithioacetals with CuCl2.
• The Chlorination of Cyclooctadiene with Cupric Chloride in Acetonitrile Containing Lithium Chloride
• The reaction of alkyl halides with mercury(II) and potassium thioacetates and selenocyanates.
• Oxidation of Isocyanides by Hg(II), Tl(III), and Pb(IV) Acetates
• Explosion during the Preparation of Ethylphenyl Thallic Acetate Perchlorate
• A convenient method for the introduction of 1,3-dithiolan-2-yl group into active methylene compounds.
• The chlorination of norbornene by metal chlorides and the product isomerization.
• Asymmetric Synthesis in the Oxymercuration Reaction Using Optically Active Mercuric Salts
• O-methylation of aromatic (E)-oximes by dimethylsulfonium methylide.
• Selenocyanatodethallation in Organothallium(III) Compounds
• Amidoselenation of Olefins Using p-Toluenesulfonamide as a Nitrogen Nucleophile.
• The chlorination of norbornadiene by various chlorinating agents.
• Chemistry of 1,3-glycol derivatives. I. The reactions of 2,4-pentanediol derivatives.
• A three-component reaction of isocyanides with halogens and cyclic ethers.
• Phenyl- and tolylthallium(III) bis(trichloroacetate)s; Preparation and reactions.
• Friedel-Crafts reaction of aromatics with epoxides. Stereochemistry and selectivities.
• Ring-opening reaction of oxiranes, oxetanes, and tetrahydropyran by mercury(II) salts and alkyl halides.
• Stereochemistry of elimination reactions of halohydrin derivatives and related compounds with butyllithium.
• The Reaction of Arylthallium(III) Compounds with Copper(II) and (I) Thiocyanates
• Medium effects on stereochemistry of acid-catalyzed ethanolysis of trans-2,3-diphenyloxirane.
• Chlorination of acyclic .BETA.-diketones. Formation and stability of .BETA.-chloro-.BETA., .GAMMA.-unsaturated ketones.
• Friedel-Crafts reactions of benzene with 1-phenylpropanols. Effects of CuCl2, Cu2Cl2, and decalin.
• Oxidation of olefins with thallium(III) acetate in diols.

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