Synthesis and lithiation of 2-alkylthio- and 2-arylthio-1,3-dithiolanes.

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概要

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• Several 2-alkylthio- and 2-arylthio-1,3-dithiolanes were synthesized by the reaction of 2-ethoxy-1,3-dithiolane with aliphatic and aromatic thiols in the presence of ZnCl<SUB>2</SUB>. The lithiation of 2-alkylthio-1,3-dithiolanes with butyllithium in tetrahydrofuran followed by the addition of alkyl halides gave unsymmetrical dialkyl trithiocarbonates in moderately good yields.

• 公益社団法人 日本化学会の論文

著者

• Tanimoto Shigeo

  Institute For Chemical Research Kyoto University Uji

• Ikehira Hideyuki

  Institute for Chemical Research, Kyoto University

• Oida Tatsuo

  Institute for Chemical Research, Kyoto University

• Okano Masaya

  Institute for Chemical Research, Kyoto University

関連論文

• 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.
• 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.
• Oxidation of Isocyanides by Hg(II), Tl(III), and Pb(IV) Acetates
• 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.
• 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.
• A three-component reaction of isocyanides with halogens and cyclic ethers.
• Phenyl- and tolylthallium(III) bis(trichloroacetate)s; Preparation and reactions.
• Ring-opening reaction of oxiranes, oxetanes, and tetrahydropyran by mercury(II) salts and alkyl halides.
• The Reaction of Arylthallium(III) Compounds with Copper(II) and (I) Thiocyanates
• Oxidation of olefins with thallium(III) acetate in diols.

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