Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Spotlight Archives
Volume 48, Issue 2
Displaying 1-8 of 8 articles from this issue
  • Yoshie SOUMA, Hiroshi SANO, Hideaki MIWA, Hiroshi KAWASAKI, Osamu ICHI ...
    1990 Volume 48 Issue 2 Pages 92-101
    Published: February 01, 1990
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Copper (I) and silver carbonyl catalysts were prepared in strong acids such as sulfuric acid, hydrogen fluoride, boron trifluoride-hydrate and fluoro sulfuric acid. Carbonylation of olefins, alcohols, dienes, diols, aldehydes and saturated hydrocarbons were carried out under atmospheric pressure and at room temperature by using copper (I) carbonyl catalyst, and tert-carboxylic acids were prepared in high yield.
    The highly hindered carboxylic acid was prepared from isobutylene oligomer. The industrial process of highly hindered carboxylic acid was established by using sulfuric acid-phosphoric acid-water mixed solvent in the recycle use of catalyst, and pilot plant started in 1988. This carbonylation method is available to the production of another compound also.
    The derivatives of highly hindered carboxylic acid is stable to hydrolysis and heat. The usages of this hindered carboxylic acid are paint, microgel, surfactant, stabilizer, initiator of polymerization, agricultural chemicals.
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  • Osamu YONEMITSU, Noriyuki NAKAJIMA, Masataka HIKOTA
    1990 Volume 48 Issue 2 Pages 102-118
    Published: February 01, 1990
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    In order to establish a simple common methodology for the highly stereoselective and efficient synthesis of macrolide aglycones, 12-membered ring methynolide and 16-membered ring tylonolide were synthesized from D-glucose via the synthesis of respective fragments followed by their coupling (esterification by the Yamaguchi method) and cyclization by the Wittig-Horner reaction under Nicolaou's conditions. This method was extended to the synthesis of 14-membered ring pikronolide and, together with conformational control of macrolide rings, to some typical 16-membered ring aglycones such as carbonolides, leuconolides, maridonolides, etc. A new synthesis of erythronolide A via an extremely efficient macrolactonization by virtue of conformational control and super activation of the seco-acid is also described.
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  • Hiroshi YAMACHIKA, Masayoshi MINAI, Kenji SAITO
    1990 Volume 48 Issue 2 Pages 119-131
    Published: February 01, 1990
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Intramolecular rearrangement of furfuryl alcohols and the following isomerization gives cyclopentenolones. These reactions were successfully applied to the syntheses of industrially valuable cyclopentenolones : allethrolone, propargyl cyclopentenolone (alcohol moiety of pyrethroids), jasmones, and intermediates of prostaglandins. Furthermore, optically active cyclopentenolones were obtained by enzyme-catalyzed enantioselective hydrolysis.
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  • Hitoshi TAKESHITA, Akira MORI, Guan Rong TIAN
    1990 Volume 48 Issue 2 Pages 132-143
    Published: February 01, 1990
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    2, 3-Bis (methoxycarbonyl) -7-oxanorbornadiene, a synthon equivalent to acetylene, reacted efficiently with anthracenes, tropones, cyclohepta [b] furan-2-ones, and cyclohepta [b] pyrrol-2 (1 H) -ones under high-pressure conditions to give cycloadducts. These adducts were thermolyzed to furnish cage-molecules such as dibenzobarrelenes, janusenes, and homobarrelenones. In the cases of cyclohepta [b] furan-2-ones and cyclohepta [b] -pyrrol-2 (1 H) -ones, [4+2] cycloadditions were predominated over [8+2] cycloadditions. The preferred cycloaddition modes were explained by a molecular orbital consideration involving the interactions of not only frontier orbitals but also NHOMO and NLUMO of dienes.
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  • Mitsuru UEDA
    1990 Volume 48 Issue 2 Pages 144-156
    Published: February 01, 1990
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    This paper reviews the synthesis of condensation polymers by the direct polycondensation. First, the concept of the direct polycondensation and the molecular design of activating agents are described, then it is demonstrated that the direct polycondensation of dicarboxylic acids with aromatic diamines using these activating agents in the presence of triethylamine proceeds at room temperature to produce polyamides with high molecular weights. Second, these activating agents are used successfully for the chemoselective polyamidation ; that is, the polyamide synthesis from dicarboxylic acids and diamines containing various functional groups are prepared without special protection of acyl-sensitive groups, and for the sequential polyamidation ; the synthesis of regular polyamides from a symmetric (YccY) and a nonsymmetric (XabX) monomers. Finally, phosphorus pentoxide-methanesulfonic acid (PPMA) is shown to be a very useful dehydrating agent for the preparation of various condensation polymers, such as poly (ether-sulfone), poly (ether-ketone) s and heterocyclic polymers.
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  • Masashi KIKUCHI
    1990 Volume 48 Issue 2 Pages 157-163
    Published: February 01, 1990
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The amination of leucoquinizarin was studied from the viewpoint of kinetics. The amination of quinizarin was also examined. The reaction behavior largely depended on the reaction conditions.
    The amination of naphthazarin was examined. Their structures and properties of leuco compounds of anthraquinones and naphthoquinones were examined and applied for human hair dyes.
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  • Hideo WAKABAYASHI
    1990 Volume 48 Issue 2 Pages 164-166
    Published: February 01, 1990
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
  • [in Japanese], [in Japanese], [in Japanese], [in Japanese]
    1990 Volume 48 Issue 2 Pages 167
    Published: February 01, 1990
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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