Chemistry of 1,3-glycol derivatives. I. The reactions of 2,4-pentanediol derivatives.
スポンサーリンク
概要
- 論文の詳細を見る
Cyclic orthoacetates of <I>meso</I>- and <I>dl</I>-2,4-pentanediol (<I>cis</I>- and <I>trans</I>-2-ethoxy-2,4,6-trimethyl-1,3-dioxane, <B>1)</B> were prepared and characterized by NMR. The stereochemical courses of the reactions of <B>1</B> with water, hydrogen chloride, trityl chloride, and acetic acid were investigated. The reactions with water gave 4-acetoxy-2-pentanol (<B>4</B>) with complete retention of configuration, while those with the other reagents gave 4-acetoxy-2-chloropentane (<B>3</B>) and 2,4-diacetoxypentane with complete inversion. Acetolyses of <B>3</B> and the tosylate of <B>4</B> gave 2,4-diacetoxypentane predominantly with retention in the absence of water. Hydrolysis of the tosylate gave <B>4</B> with almost complete inversion. These results can be explained by the mechanism that the reactions proceed mainly through acetoxonium cation intermediate involving six-membered ring. The fluoroborate salt of this acetoxonium cation was prepared and characterized by NMR.
- 公益社団法人 日本化学会の論文
著者
-
Ichikawa Katsuhiko
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
-
Itoh Osamu
Department of Chemistry, The University of Tsukuba
-
Ichikawa Yasunori
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
-
Katano Hiroaki
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
関連論文
- Mixed Connective Tissue Disease with Severe Pulmonary Hypertension and Extensive Subcutaneous Calcification
- Photoneutron Cross Sections for Au Revisited : Measurements with Laser Compton Scattering γ-Rays and Data Reduction by a Least-Squares Method
- Syntheses of aryl glyoxylate. I. The reaction of alkyl dichloro(alkoxy)acetates with aromatics in the presence of Lewis acid.
- The Chlorination of Cyclooctadiene with Cupric Chloride in Acetonitrile Containing Lithium Chloride
- Explosion during the Preparation of Ethylphenyl Thallic Acetate Perchlorate
- Asymmetric Synthesis in the Oxymercuration Reaction Using Optically Active Mercuric Salts
- Selenocyanatodethallation in Organothallium(III) Compounds
- Intermolecular Pummerer rearrangement reactions of alkyl phenyl and dialkyl sulfoxides with acetic anhydride.
- Chemistry of 1,3-glycol derivatives. I. The reactions of 2,4-pentanediol derivatives.
- Phenyl- and tolylthallium(III) bis(trichloroacetate)s; Preparation and reactions.
- Friedel-Crafts reaction of aromatics with epoxides. Stereochemistry and selectivities.
- 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.