Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Volume 47, Issue 7
Displaying 1-8 of 8 articles from this issue
  • Yoshio ITO, Shiro TERASHIMA
    1989 Volume 47 Issue 7 Pages 606-618
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The 1β-methylcarbapenem antibiotics represented by 3, 4, and 5, have been the focus of current synthetic endeavor due to prominent antibacterial activities and broad spectra as well as enhanced chemical and metabolic stability. Progress of the syntheses of 1β-methylcarbapenem key intermediates represented by 6, are reviewed based on the synthetic methods of the characteristic 1β-methyl substituent involved in the contiguous four chiral centers of 6.
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  • Diazotization-Fluorodediazoniation of Aminoaromatics
    Norihiko YONEDA, Tsuyosi FUKUHARA
    1989 Volume 47 Issue 7 Pages 619-628
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Fluoro-dediazoniation of aromatic diazonium salts, derived from diazotization of amino aromatics, is the most usual means of introducing a fluorine substituent into aromatic rings. But they are not without difficulties. Thus the recent progress and development of entire process is reviewed.
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  • Koki NAKAMURA, Keizo KOYA, Kozo SATO
    1989 Volume 47 Issue 7 Pages 629-635
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Ring opening reactions of 2-nitroaryl-4-isoxazolin-3-ones have been studied. N-O bond of 2-nitroary1- 4-isoxazolin-3-ones was cleaved by mild organic reducing agents. The N-O bond cleavage is presumably caused by an electron transfer into 2-nitroaryl group of 4-isoxazolin-3-ones.
    2-Nitroaryl-4-isoxazolin-3-ones are very easy to synthesize and widely applicable because an introduction of CH2L (L=leaving group) at 4-position of isoxazoline makes it possible to release a functionalized group.
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  • Takahiro HOSOKAWA, Shun-ichi MURAHASHI
    1989 Volume 47 Issue 7 Pages 636-648
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The functionalization of alkenes with oxygen nucleophiles is attained by a process being referred to as oxypallation which involves nucleophilic attack toward alkenes co-ordinated to Pd (II). In reactions of this type (the Wacker-type reaction), the redox catalysis of palladium and copper (eqs 1 and 2) has been believed to regenerate Pd (II) from Pd (O) formed in situ. This article describes that the catalysis is not generally operative, but that a hydroperoxopalladium (II) species (XPdOOH) coupled with CuXn is most likely the active catalyst which is formed by the oxygenation of XPdH liberated from oxypalladation adduct. This finding has been deduced from the analysis of Pd (II) -catalyzed asymmetric cyclization of 2- (2-butenyl) phenol, which is the first example of the asymmetric Wacker-type oxidation. Furthermore described is the new aspect of the following Wacker-type reactions ; (i) intramolecular oxidative cyclization of alkenes bearing hydroxy group and (ii) acetalization of terminal alkenes with diols. These reactions have synthetic potential for preparing optically active heterocyclic compounds such as (S) - (+) -tremetone and (S) - (-) -frontaline.
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  • Jiro TSUJI, Junzo NOKAMI, Tadakatsu MANDAI
    1989 Volume 47 Issue 7 Pages 649-659
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Recent advances in the oxidation reactions of olefins catalyzed by Pd2+ salts, and the scope and limitations of the reaction are surveyed. Emphasis is placed on the oxidation of terminal olefins with various functional groups to methyl ketones. Useful applications of this reaction to syntheses of various natural products such as steroids, terpenoids are shown. Internal olefins are oxidized to ketones smoothly with high regioselectivity only when there is a good participation of neighbouring oxygen functions.
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  • Kazuko MATSUMOTO
    1989 Volume 47 Issue 7 Pages 660-668
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Since the first report in 1908, a class of platinum compounds called “platinum blues” have attracted interests of chemists because of their unusual dark blue color. However, because of the difficulty in isolating and crystallizing the complexes, their formulas and structures have been left unclarified till a decade ago. About ten years ago when it turned out that the famous anti-tumor complex cis-Pt (NH3) 2CL2 effects its activity by binding to DNA and obstructing the DNA duplication, a study regarding the coordination reaction of cis-Pt (NH3) 2Cl2 with pyrimidine bases started and the platinum pyrimidine blues found in the study again aroused interest of chemists. In the course of intensive studies, the first crystal structure determination of platinum blue was carried out for a compound with α-pyridone as a pyrimidine model and the tetranuclear 5+ mixed-valent chain structure of [Pt4 (NH3) 8 (C5H4NO) 4] was revealed.
    In the present article, syntheses, structures and chemical properties of platinum blues and several other related multinuclear platinum complexes containing hetero metal atoms are surveyed with an emphasis on the specific nature of amidate ligands that stabilize unusually high oxidation state of metals.
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  • Junichi SHIRAOGI
    1989 Volume 47 Issue 7 Pages 669-670
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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  • [in Japanese], [in Japanese], [in Japanese], [in Japanese], [in Japane ...
    1989 Volume 47 Issue 7 Pages 671
    Published: July 01, 1989
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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