Studies on Acetylenic Compounds. XLVII. The Rearrangement of Acetylenic Sulfonium Salts

スポンサーリンク

概要

• 論文の詳細を見る

• Treatment of acetylenic sulfonium salts, dimethyl 3-phenyl-2-propynylsulfonium bromide (VII), dimethyl 2-butynylsulfonium bromide (XII) and methyl bis (3-phenyl-2-propynyl) sulfonium methyl sulfate (XIX), with base gave SNi'reaction products, methyl 2-phenyl-2,3-butadienyl sulfide (VIII), methyl 2-methyl-2,3-butadienyl sulfide (XIII) and methyl 1-(2-phenylethynyl)-2-phenyl-2,3-butadienyl sulfide (XXII), respectively. Similarly, methyl (2-propenyl) (3-phenyl-2-propynyl) sulfonium methyl sulfate (XXIII) was converted to methyl 1-(2-phenylethynyl)-3-butenyl sulfide (XXVII) by SNi'reaction. The reaction of methyl benzyl 3-phenyl-2-propynylsulfonium methyl sulfate (XXXIII) with base, however, afforded the usual Stevens type rearrangement product, methyl 1-benzyl 3-phenyl-2-propynyl sulfide (XXXVI). A mechanistic assumption for the rearrangements of acetylenic sulfonium salts was given.

• 公益社団法人日本薬学会の論文
• 1969-05-25

著者

• 岸田 有吉

  Central Research Laboratories Sankyo Co. Ltd.

• 寺田 敦祐

  Central Research Laboratories, Sankyo Co., Ltd.

• 寺田 敦祐

  京都薬科大学 化学研究所

関連論文

• Studies on Acetylenic Compounds. LVI. Syntheses of 4-Isoxazolin-3-ones and 1-Phenyl-3-hydroxypyrazoles
• The Addition Reaction of Diethyl Acetamidomalonate Anion to Ethyl α, β-Dibromoacrylate, and the Base-catalyzed Reactions of the Adduct
• Studies on Acetylenic Compounds. XLIII. Synthesis of Ibotenic Acid.
• Studies on Acetylenic Compounds. XLIII. Synthesis of Ibotenic Acid
• Stereospecific Taurine Conjugation of the trans-OH Metabolite (Active Metabolite) of CS-670,a New 2-Arylpropionic Acid Nonsteroidal Anti-inflammatory Drug, in Dogs
• プロフェン系抗炎症薬CS-670のイヌにおける立体特異的タウリン抱合
• Studies on 1,3-Benzoxazines. III. Reaction of Imidoyl Chlorides of 1,3-Benzoxazines with 2-Hydroxy- or 2-Mercaptopyridine N-Oxides : A Novel S-N Bond Formation via Electrocyclic Rearrangement
• Determination of Configurations of the Two DL-Isomers of 1-(p-Nitrophenyl)-3-(2,2-dichloroacetamido)-1,2-propanediols.
• Syntheses of 1-(p-Nitrophenyl)-3-(2,2-dichloroacetamido)-1,2-propanediols.
• Reactivities of 4-Arylthio-2-azetidinones
• Syntheses of 2-Azetidinone (β-Lactam) Ring by Chlorosulfonyl Isocyanate (CSI)
• Studies on Acetylenic Compounds. LIX. Reactions of Acetylene Sulfonium Ylids with α, β-Unsaturated Esters
• Studies on Seven-membered Ring Compounds. XXXVII. The Reaction of Benzotropones with Malononitrile
• Studies on Acetylenic Compounds. LVIII. Reaction of 2-Propynyl Sulfones with Methyl Acrylate
• Chemistry of 2-Substituted Thiothiazoline. V. Reaction of Dianion of 2-Propargylthiothiazoline with Benzaldehyde
• Syntheses of 5,5'-Methylenebisisoxazole Derivative and Its Reactions with Electrophiles
• Syntheses and Reactions of 2-Substituted Thiazolidines
• Reactions of β-Keto Sulfide and Sulfoxide with Nitrene and Diazonium Salt
• Studies on Acetylenic Compounds. LVII. Reactions of 2-Propynyl Sulfones with Cyclic Ketones
• Syntheses of Novel Acetylene Cyclopropanes
• Use of a Shift Reagent in First-Order Analysis of Cyclopropane Derivatives in NMR Spectroscopy
• Studies on Acetylenic Compounds. LV. Reactions of Phenyl 2-Propynyl Sulfone and Phenyl 3-Phenyl-2-propynyl Sulfone with Substituted Benzaldehydes
• Studies on Acetylenic Compounds. LIV. Reactions of 2-Butynyl Phenyl Sulfone with Substituted Benzaldehydes
• Studies on Acetylenic Compounds. LIII. The Reactions of Acetylenic Sulfonium Salts with Acid Anhydride or Acid Chloride
• Reactions of Enamino Ketones and an Enamino Ester with Some Electrophiles
• Studies on Acetylenic Compounds. LII. Reactions of Acetylenic Sulfonium Salts with Cyclohexanone and Cyclopentanone
• Rearrangements and Reactions of Stable Sulfonium Ylids from Acetylenic Sulfonium Salts
• Studies on Acetylenic Compounds. LI. The Reactions of Acetylenic Sulfonium Salts with Benzaldehyde
• Studies on 1,3-Benzoxazines. VII. Formation of Diphenylpyrimidines by the Reaction of 4-Chloro-2H-1,3-benzoxazines with Ethyl 3-Aminobutyrate
• Studies on 1,3-Benzoxazines. VI. Formation of Quinazolines and 4H-3,1-Benzoxazines by the Reaction of 4-Chloro-2H-1,3-benzoxazines with Aminoacetophenone, Aminobenzophenone and Aminobenzyl Alcohol Derivatives
• Reactions of 2-Piperidylacetohydrazides with Ethyl Acetoacetate or Acetylenic Acid Esters. Formation of 3,4-Dimethylpyrano-[2,3-c] pyrazol (6) ones and Perhydropyrazolo [2,3-a]-pyrido [1,2-c] pyrimidin-2,5-diones
• Studies on Benzodiazepinooxazoles. V. Reactions of Benzo [6,7]-1,4-diazepino [5,4-b] oxazole Derivatives with Acetic Anhydride
• Studies on Benzodiazepinooxazoles. IV. The Formation of Quinolones by the Ring Contraction of a Benzo [6,7]-1,4-diazepino [5,4-b]-oxazole Derivative
• Studies on Benzodiazepinooxazoles. III. Reactions and Rearrangements of Benzo [6,7]-1,4-diazepino-[5,4-b] oxazole Derivatives
• 7-Aza-5β-cholestane Derivatives
• Sulfoxonium Ylide Chemistry. III. The Photochemistry of Stable Sulfoxonium Ylides
• Sulfoxonium Ylide Chemistry. II. Reaction of Stable Sulfoxonium Ylides with Base
• Studies on Acetylenic Compounds. XLIV. Sulfoxonium Ylide Chemistry. I. Formation of Stable Sulfoxonium Ylides from Acetylenic Compounds
• Formation of Thiabenzene 1-Oxide Derivatives
• Optical Resolution of (±)-2-[4-(2-Oxocyclohexylidenemethyl)phenyl]propionic Acid
• Synthesis of the Eight Possible Optically Active Isomers of 2-[4-(2-Hydroxycyclopentylmethyl) phenyl] propionic Acid
• Optical Resolution and Determination of Absolute Configuration of (±)-2-[4-(2-Oxocyclopentylmethyl) phenyl] propionic Acids
• Studies on 1,3-Benzoxazines. II. New Rearrangement Modes in the Reaction of 4-Chloro-2,2-dimethyl-2H-1,3-benzoxazine with Substituted Pyridine N-Oxides
• Formation of Triazole and Isoxazole Derivatives from β-Substituted Pyridinium Salts
• Formation of Pyrazole Derivatives from β-Substituted Pyridinium Salts
• Studies on 1,3-Benzoxazines. I. Synthesis of Primary 2-Aminopyridines via the Reaction of Imidoyl Chlorides of 1,3-Benzoxazines with Pyridine N-Oxides
• Opitical Resolution and Determination of Absolute Configuration of 2-(2-Isopropylindan-5-yl) propionic Acid
• Bischler-Napieralski Reactions of N-(2-Indolylethyl) acetamide
• Reactions of Azlactone Derivatives with Nucleophiles and Acetylenic Compounds
• Studies on Acetylenic Compounds. L. The Formation of Stable Sulfonium Ylids from Acetylenic Sulfonium Salts
• The Reactions of Ethyl cis-β-Chloroacrylate with Aminomalonate Derivatives
• Studies on Acetylenic Compounds. XLVIII. The Reactions of Allenic and Acetylenic Sulfides with Methyl Iodide
• Studies on Acetylenic Compounds. XLVII. The Rearrangement of Acetylenic Sulfonium Salts
• Studies on Acetylenic Compounds. XLVI. The Reactions of Acetylenic Compounds with Thiourea or Ammonium Dithiocarbamate
• On the Absolute Configuration of Natural 24-Alkylsterols.

もっと見る 閉じる

スポンサーリンク