Studies on Telomers and Oligomers of Vinylene Carbonate. VI. Stereoselective Conversion of Vinylene Carbonate Telomers to trans Unsaturated Phosphate Esters and Their Chemical Behaviors
スポンサーリンク
概要
- 論文の詳細を見る
Smooth conversion of telomers of vinylene carbonate with carbon tetrachloride or methylene bromide as a telogen to novel trans enol phosphates, and the reactivities of the phosphates thus formed are described. Both trans-"anti"-trans- and trans-"syn"-trans-isomers of the n=2 telomers, 5-chloro-5'-trichloromethyl-(4,4'-bi-1,3-dioxolan)-2,2'-dione and 5-bromo-5'-dibromomethyl-(4,4'-bi-1,3-dioxolan)-2,2'-dione gave, on treatment with trialkyl phosphites, the identical trans dialkyl 2-(5-trichloromethyl- and 2-(5-dibromomethyl-2-oxo-1,3-dioxolan-4-yl) vinyl phosphates in good yields, without any detectable amount of cis isomer and the phosphonate, while the n=1 adduct failed to give the corresponding enol phosphate. Stereospecific conversion of the phosphate to cis 2-(5-trichloromethyl-2-oxo-1,3-dioxolan-4-yl) vinyl acetate was readily achieved by new vinylic exchange reaction catalyzed by palladium chloride in acetic acid by way of the processes, trans oxypalladation and trans deoxypalladation. Reactions involving catalytic hydrogenation, chlorination with titanium chloride and conversion to α, β-unsaturated aldehydes are summarized in Chart 2.
- 社団法人日本薬学会の論文
- 1977-02-25
著者
-
滝沢 武夫
Faculty of Pharmaceutical Sciences, University of Tokyo
-
国枝 武久
Faculty of Pharmaceutical Sciences, University of Tokyo
-
松浦 勉
Faculty Of Pharmaceutical Sciences University Of Tokyo
-
滝沢 武夫
Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address) Department Of Chemistry Uni
-
国枝 武久
Faculty Of Pharmaceutical Sciences Kumamoto University
関連論文
- Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters
- Facile Conversion of 4-Halogeno-1,3-dioxolan-2-ones to 2-Oxazolidones
- Studies on Telomers and Oligomers of Vinylene Carbonate. VII. Facile Synthesis of Trihalogenomethyl-containing Aldo-sugars and Polyalcohols
- Studies on Telomers and Oligomers of Vinylene Carbonate. VI. Stereoselective Conversion of Vinylene Carbonate Telomers to trans Unsaturated Phosphate Esters and Their Chemical Behaviors
- Studies on Telomers and Oligomers of Vinylene Carbonate. V. Preparation and Stereochemistry of Adducts of Vinylene Carbonate with Tribromomethyl Compounds as Potential Intermediates for Sugar-like Compounds
- 3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxycarbonylation and Benzyloxycarbonylation of Amino Groups
- "INVERSE"TYPE OF SYNTHETIC INHIBITORS OF TRYPSIN, S-ω-AMINOALKYL THIOESTERS
- Thermal Equilibrations of 1,11-Dioxa [11] paracyclophane Derivatives in Cholesteric Liquid Crystals
- 有機合成におけるカルボキシル基の活性化
- アボット奨学金によるアメリカ研修旅行
- Facile Desulfurization of Thiocarbonyl Groups to Carbonyls by Superoxide. A Model of Metabolic Reactions
- Epimerization of Aldoses Catalyzed by Dioxobis (2,4-pentanedionato-O, O')-molybdenum (VI). An Improved Procedure for C-2 Epimer Preparation
- A NEW NITRATION PRODUCT, 3-NITRO-4-ACETAMIDOPHENOL, OBTAINED FROM ACETAMINOPHEN WITH NITROUS ACID
- Iron Carbonyls as Mild Friedel-Crafts Catalytic Agent
- Telomers (n=3) of Vinylene Carbonate with Tetrachloromethane as Novel Synthetic Intermediates for Aldo-heptoses and -octoses
- Convenient Preparation of Tetraarylbutatrienes
- Mild Dehalogenative Reduction of Tri- and Di-halogenomethyl Compounds to Lower Halides by Nickel Tetracarbonyl
- ビニレンカルボナ-ト低級テロマ-の合成と反応
- Studies on Indole Series.I.Studies on the Synthesis of Optically Active Indole Derivatives
- Studies on Optical Rotatory Dispersion and Circular Dichroism.I.Absolute Configuration of Cyclic α-Amino-ketones and Octant Rule
- Studies on Optically Active Amino Acids.XIII.Racemization of N-Benzoylanilides of Optically Active Proline and Pipecolic Acid
- Studies on Optically Active Amino Acids. XII.Synthesis, Resolution and Racemization of Bicyclic α-Amino-ketones
- Chemistry of Sodium Borohydride and Diborane. III. Synthesis of (+)-Lupinine by Hydroboration Reaction
- Stereoselective Preparation of (1S, 2R)- and (1S, 2S)-2-Hydroxy-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic Acids
- New Synthetic Routes to Carbohydrates by the Use of Telomers of Vinylene Carbonate with Polyhalomethanes
- Studies on Cyclic vic-Polyketones. I. Syntheses and Characterization of 1,2-Disubstituted Cyclopentenetriones
- Oxidative Cleavage of Indoles using Copper-Pyridine Complex
- Reactions of N-(p-Toluenesulfonyl)-diphenylcyclopropenimine with Trivalent Phosphorus Compounds
- Reactions of Diphenylcyclopropenone with Trivalent Phosphorus Compounds
- Reaction of Isocyanide-Mercuric Chloride Complexes with Active Methylene Compounds
- ビニレンカルボナート低級テロマーの合成と反応