Amidoselenation of Olefins Using p-Toluenesulfonamide as a Nitrogen Nucleophile.
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概要
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The reaction of olefins, benzeneselenenyl chloride, and <I>p</I>-toluenesulfonamide in the presence of zinc(II) chloride affords <I>N</I>-[2-(phenylseleno)alkyl]-<I>p</I>-toluenesulfonamides in good to excellent yields. When combined with alkylation on the carbon atom bearing the phenylseleno group thus introduced and subsequent oxidative or reductive removal of the selenium moiety, this reaction can be utilized in the preparation of a wide range of allylic or saturated amides.
- 公益社団法人 日本化学会の論文
著者
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Toshimitsu Akio
Institute For Chemical Research Kyoto University
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Tanimoto Shigeo
Institute For Chemical Research Kyoto University Uji
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Oida Tatsuo
Institute for Chemical Research, Kyoto University
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Kusumoto Takehiro
Institute for Chemical Research, 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.
- The reactions of olefins with chloromethoxymethane or dimethoxymethane in nitriles.
- Diphenylsilane reduction of C=O and C=N bearing electron-withdrawing group in the presence of aluminum(III) chloride.
- The formation of 1,2-bis(alkylthio)-1,2-diphenylethanes by the lithium diisopropylamide-induced fragmentation of dibenzyl disulfide followed by the trapping with some alkyl halides.
- Synthesis and lithiation of 2-alkylthio- and 2-arylthio-1,3-dithiolanes.
- The lithium diisopropylamide-induced fragmentation of 1,3-dithiolane derivatives of several ketones having .ALPHA.-hydrogen.
- Chlorination of acetylenes with sulfuryl chloride.
- The lithium diisopropylamide-induced fragmentation of 2,2-diphenyl-1,3-dithiolane S-oxide and several 2,2-diaryl-1,3-dithiolane S,S'-dioxides.
- The formation of vinyl sulfides by the cleavage of the carbon-sulfur bond in dithioacetals with CuCl2.
- Synthesis of 2-(trimethylsilyl)ethyl benzenesulfenate and benzeneselenenate and their reaction with some electrophiles in the presence of tetrabutylammonium fluoride.
- A new Wittig rearrangement of 2,2-disubstituted 1,3-dithianes.
- The reaction of alkyl halides with mercury(II) and potassium thioacetates and selenocyanates.
- A convenient method for the introduction of 1,3-dithiolan-2-yl group into active methylene compounds.
- O-methylation of aromatic (E)-oximes by dimethylsulfonium methylide.
- Selenocyanatodethallation in Organothallium(III) Compounds
- Amidoselenation of Olefins Using p-Toluenesulfonamide as a Nitrogen Nucleophile.
- A three-component reaction of isocyanides with halogens and cyclic ethers.
- Oxidation of olefins with thallium(III) acetate in diols.