Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Volume 46, Issue 10
Displaying 1-8 of 8 articles from this issue
  • Shun-Ichi MURAHASHI, Takeshi NAOTA
    1988 Volume 46 Issue 10 Pages 930-942
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Organic synthesis using stoichiometric and catalytic amounts of ruthenium compounds are reviewed with an emphasis on the recent progress. The present article surveys on the following subjects, i) hydrogenation, ii) oxidative transformation, iii) isomerization of olefins, iv) nucleophilic addition to carbon-carbon and carbonnitrogen multiple bonds, v) radical reaction, vi) dimerization and condensation reaction, and vii) reaction with carbon monoxide and carbon dioxide.
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  • Junji ICHIKAWA, Hiroshi KOBAYASHI, Takaaki SONODA
    1988 Volume 46 Issue 10 Pages 943-954
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Tetrakis [3, 5-bis (trifluoromethyl) phenyl] borate (TFPB), a highly lipophilic fluoroaromatic borate ion which is remarkably stable under acid and oxidative conditions, was designed as an anionic phase-transfer catalyst, whose function is to transfer cationic species such as diazonium and oxonium ions in reactive form of ion pair from an aqueous (or solid) phase into a nonpolar organic phase and to promote catalytically the electrophilic reactions in two-phase systems. Some effecive examples of anionic phase-transfer catalysis (PTC) with TFPB were demonstrated in the diazo coupling, the Friedel-Crafts alkylation, the nitrosation (in situ diazo coupling), the acid-mediated hydrolysis of esters, and the redox reactions with methylviologen in liquid membrane system. Kinetic investigations of these PTC reactions clearly indicated that the enhanced reactivities of the cationic species and the specificities of the electrophilic reactions were due to the dehydration of such cationic species ion-paired with TFPB in nonpolar organic phase.
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  • Kazuhiro NAKASUJI, Mitsuru SASAKI, Ichiro MURATA
    1988 Volume 46 Issue 10 Pages 955-969
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The scientific progresses in the organic molecular metals based on tetrathiafulvalene (TTF) type donors offer three general strategies for molecular design : (1) construction of new multi-stage redox systems, (2) chemical modifications to introduce interstack interactions, and (3) control of degree of charge transfer (CT) According to such strategies, we have recently synthesized peri-condensed Weitz type donors as new multistage redox systems, 3, 10-dithiaperylene (DTPR), 1, 6-dithiapyrene (DTPY), and methylthio and ethylenedithio derivatives of DTPY (MTDTPY, ETDTPY) These new donors produced a variety of CT complexes. An important finding is the realization of organic molecular metals having donors and acceptors outside the TTF and TCNQ (tetracyanoquinodimethane) type components. Not only some physical properties of these new molecular conductors but also some basic features for organic conductors from the organic chemistry point of view are presented.
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  • Yoshihiko MORO-OKA, Wataru UEDA
    1988 Volume 46 Issue 10 Pages 970-976
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    A novel C-C bond formation to form α, β-unsaturated compounds has been developed by using methanol as a methylenylating agent. Methyl or methylene group at a-position of saturated ketones, esters or nitriles is converted to vinyl group by addition of methanol accompanied by both dehydrogenation and dehydration. The reaction is effectively promoted by magnesium oxide catalysts activated by transition metal cations.
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  • Keiichi UCHIDA, Hiroki TANAKA
    1988 Volume 46 Issue 10 Pages 977-985
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Some amino acids are synthesized effectively by enzymatic reactions. These enzymatic reactions are also applicable to the synthesis of optically active fluorine-containing amino acids by the use of corresponding fluorine-containing precursors.
    This paper describes the following enzymatic reactions. 1) Synthesis of fluorine-containing phenylalanines by transamination of corresponding fluorine-containing phenylpyruvic acids, by phenylalanine ammonia-lyase reaction of fluorine-containing t-cinnamic acids, and by acylase reaction of fluorine-containing N-acetyl phenylalanines, 2) synthesis of fluorotyrosines by β-tyrosinase starting from fluorophenols and serine, 3) synthesis of fluorotryptophan by tryptophanase starting from fluoroindole and serine.
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  • Shoji KAJIGAESHI, Takaaki KAKINAMI
    1988 Volume 46 Issue 10 Pages 986-989
    Published: 1988
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Benzyltrimethylammonium tribromide (BTMA Br3), a stable solid brominating agent, can be prepared by the reaction of benzyltrimethylammonium chloride with sodium bromate and hydrobromic acid in aqueous solution. In this article, the useful synthetic applications of BTMA Br3 are described. The reactions of aromatic compounds such as phenols, aromatic amines, aromatic ethers and acetanilides with BTMA Br3 in dichloromethane-methanol at room temperature give easily bromo-substituted products in good yields, respectively. On the reaction of arenes with BTMA Br3, electrophilic.bromination occurs in acetic acid in the presence of zinc chloride, and benzylic brominatlon proceeds in refluxing benzene in the presence of AIBN. Furthermore, BTMA Br3 reacts with acetyl derivatives to give dibromoacetyl derivatives, and with alkenes to give 1, 2-dibromo adducts.
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  • Haruo SAKAI
    1988 Volume 46 Issue 10 Pages 990-991
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
  • [in Japanese], [in Japanese]
    1988 Volume 46 Issue 10 Pages 992
    Published: 1988
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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