Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Volume 37, Issue 12
Displaying 1-19 of 19 articles from this issue
  • Synthesis and Properties of Organolithium, -sodium and -potassium Compounds
    Tamejiro HIYAMA
    1979 Volume 37 Issue 12 Pages 982-990
    Published: December 01, 1979
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    The general features of organolithium, -sodium and -potassium compounds are reviewed particularly with the emphasis on their stability and reactivity. Successively, experimental procedures for the synthesis of these organometallic reagents are summarized. Finally discussed is the preparation of metal amides.
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  • Preparation of Copper Compounds Utilized for Organic Syntheses
    Yoshihiko ITO
    1979 Volume 37 Issue 12 Pages 991-995
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Lithium dialkylcopper, cuprate, is prepared in situ by treating a suspension of cuprous iodide in ether or THF with 2 equivalent of alkyllithium. Anhydrous cupric chloride is prepared by heating commercially available CuCl2·2H2O at 120°C for several hours. Cuprous oxide is prepared by heating commercially available Cu2O in vacuo at 6070°C for several hours. Copper (I) carbonyl cation is generated by treating cuprous oxide in sulfuric acid with 1 atm. of carbon monoxide. Active copper powder is prepared by reducing cupric sulfate in water with zinc powder under nitrogen gas. Copper (I) tert-butoxide is prepared by reacting anhydrous cuprous chloride with lithium tert-butoxide in THF. Copper (I) tert-butoxide is thermally stable under nitrogen and purified by sublimation at 170°C/1 mmHg. Copper (I) triflate · (benzene) 1/2 complex is prepared by heating cuprous oxide with trifluoromethanesulfonic acid anhydride in benzene at reflux. Some synthetic reactions using the copper compounds thus prepared are also described.
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  • Preparation and Reaction of Zinc Compounds in Organic Synthesis
    Ikuzo NISHIGUCHI
    1979 Volume 37 Issue 12 Pages 996-1000
    Published: December 01, 1979
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Recent progress of preparation and reaction of a variety of zinc compounds, such as organozinc compounds, zinc-other metal couples and activated zinc, in organic synthesis is described in this article.
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  • Organomercury and Organothallium Compounds
    Sakae UEMURA
    1979 Volume 37 Issue 12 Pages 1001-1007
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Preparation methods for 11 organomercury compounds, mercury (II) trifluoroacetate, 4 organothallium compounds, 4 inorganic thallium (III) salts, thallium (I) ethoxide, and thallium (I) t-butylthiolate have been described. The price of the chemical and the name of the company which produces it are cited, when it is commercially available. The utility of each compound for representative organic synthesis and some of their chemical and physical properties (toxicity, reactivity to air and water, melting point etc.) have also been described.
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  • Synthesis and Properties of Boron Compounds
    Yoshinori YAMAMOTO, Kazuhiro MARUYAMA
    1979 Volume 37 Issue 12 Pages 1008-1016
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Boron compounds frequently used in organic synthesis are classified into three groups; i) reducing reagents, ii) hydroborating reagents, and iii) organoboranes. Synthesis, properties, and commercial availability of these boron compounds are described. Furthermore, typical applications to organic synthesis are briefly mentioned. The compounds listed are NaBH4, NaBH2S3, NaBH3CN, LiBH3CN, Bu4NBH3CN, LiEt3BH, Li and KsecBu3BH, BH3·THF, BH3·SMe2, BH3·Amine, 9-BBN, Disiamylborane, Thexylborane, Dipinylborane, Catecolborane, BH2Cl·SMe2, BHCl2·SMe2, R3B, 9-BBN-triflate, Aminohaloborane, 3-Pinanyl-9-BBN, and Boronic Esters.
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  • Organoaluminum Compounds
    Tadamichi HIRABAYASHI
    1979 Volume 37 Issue 12 Pages 1017-1021
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The directions for use of organoaluminum compounds in the field of organic synthetic chemistry are explained with the assistance of 37 references and one table on the physical properties of major compounds which are commercially available. The general caution with respect to handling of organoaluminum compounds is also described to give the beginners.
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  • Titanium Compounds in Organic Synthesis
    Yoshio OTSUJI, Kakuzo ISAGAWA
    1979 Volume 37 Issue 12 Pages 1022-1025
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Preparation and properties of various types of titanium compounds are described, and their applications in organic synthesis are presented with practical procedures under the following three categories : the use of titanium (IV) compounds as Lewis acids, the use of low-valent titanium compounds as reducing reagents, and the use of titanium-aluminium complexes as catalysts.
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  • Synthesis and Properties of Organometallic Compounds of Silicon and Tin which are Used in Organic Synthesis
    Akira HOSOMI
    1979 Volume 37 Issue 12 Pages 1026-1033
    Published: December 01, 1979
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Synthetic procedures and notes and their properties of representative organometallic compounds of group IV B elements (Si, Sn) which are used in organic synthesis are described.
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  • Applications of (Arene) tricarbonylchromium Complexes in Organic Synthesis
    Masaaki YOSHIFUJI
    1979 Volume 37 Issue 12 Pages 1034-1036
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    (Arene) tricarbonylchromium complexes can be prepared simply by heating arenes with hexacarbonylchromium in high yield. These complexes undergo selective reactions on or adjacent to metal-complexed aromatic rings; removal of electron density from the arenes through coordination allows nucleophilic reactants to add to a carbon of the arene ring under mild reaction conditions and the bulky Cr (CO) 3 moiety can exert a large steric blocking effect causing stereo-selective reactions. Some typical experimental procedures are described.
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  • Applications of Organozirconium Complexes in Organic Synthesis
    Masaaki YOSHIFUJI
    1979 Volume 37 Issue 12 Pages 1037-1040
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Hydrozirconation using chlorobis (η-cyclopentadienyl) hydridozirconium (IV) is a useful procedure for functionalizing alkenes, alkynes, and 1, 3-dienes via organozirconium (IV) intermediates. These intermediates react with a variety of electrophilic reagents to give organic products in high yield. Via transmetalation the zirconium intermediates also serve as precursors of reactive organometallic compounds of metallic elements whose chemistry is well established with regard to C-C bond formation processes. Some typical experimental procedures are described.
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  • Molybdenum and Tungsten Compounds Utilized in Organic Synthesis
    Akira NAKAMURA
    1979 Volume 37 Issue 12 Pages 1041-1046
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    A variety of molybdenum and tungsten compounds, e. g. MoCl5, Mo (CO) 6, MCl6, W (CO) 5CR2, has been utilized as catalysts in Lewis acidic catalysis, olefin metathesis, olefin epoxidation, or as reagents in chlorination etc. Selected typical examples of these reactions are listed and properties, prices, methods of preparation, and precautions in practical uses are described.
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  • Synthesis and Properties of Selenium Compounds Used for Organic Synthesis
    Kiyoshi KONDO, Noboru SONODA
    1979 Volume 37 Issue 12 Pages 1047-1052
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Synthesis and properties of several useful selenium compounds are described.
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  • The Preparation and Reactions of Tetracarbonylferrates
    Yoshihisa WATANABE
    1979 Volume 37 Issue 12 Pages 1053-1058
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Various tetracarbonylferrates including potassium tetracarbonylhidrido-, tetramethylammonium tetracarbonylhydrido-, disodium or dipotassium tetracarbonyl-ferrate can be prepared from pentacarbonyliron and bases or reducing agents by different methods. All these ferrates are widely used as effective reducing and carbonylating agents in organic synthesis.
    Several reactions of dieneirontricarbonyls are also described.
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  • Ruthenium and Osminum Compounds
    Hideyuki MATSUMOTO
    1979 Volume 37 Issue 12 Pages 1059-1064
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    This article deals chiefly with low-valent ruthenium- and osmium-phosphine complexes and presents a brief review of their available methods of synthesis with preparative examples. Also described are the recent examples of their use in homogeneous catalysis.
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  • Syntheses of Cobalt Complexes
    Hiroshi YAMAZAKI, Yasuo WAKATSUKI
    1979 Volume 37 Issue 12 Pages 1065-1071
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Syntheses and properties of the following nine selected cobalt complexes which are of importance in the catalytic and stoichiometric syntheses of organic compounds are described : octacarbonyldicobalt, tetracarbonylhydridocobalt, sodium tetracarbonylcobaltate, μ-acetylenehexacarbonyldicobalt, alkylidynenonac arbonyltricobalt, dicarbonyl-η-cyclopentadienylcobalt, bis (η-cyclopentadienyl) cobalt, hydridodinitrogentris (triphenylphosphine) cobalt and η-cyclopentadienyltriphenylphosphine (cobaltacyclopentadiene).
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  • Rhodium and Iridium Compounds
    Takamichi YAMAGISHI
    1979 Volume 37 Issue 12 Pages 1072-1080
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Since the prominent application of the Wilkinson complex to the hydrogenation of olefins, many organic reactions catalyzed by rhodium complexes and iridium analogs have been reported. In this review, the preparative methods, properties of rhodium compounds and their applications to organic synthesis as well as those of iridium compounds are described. Rhodium and iridium compounds are generally prepared starting from their water-soluble halogeno compounds such as RhCl3·3H2O or IrCl3H2O. The oxidation state of the compounds obtained is strongly dependent on the nature of the ligands. Low-valent (from -3 to zero) complexes are stabilized by carbon monoxide which behaves as a strong π-acceptor. Uni-valent complexes are coordinated by olefins, dienes, carbon monoxide, phosphines, arsines or amines. Most of low-valent complexes are air-sensitive and should be handled under inert atmosphere. They easily undergo the oxidative addition reaction and catalyze organic reactions, such as hydrogenation, hydrosilylation, hydroformylation, oligomerization, isomerization, carbonylation, decarbonylation, etc.
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  • Nickel
    Kohei TAMAO
    1979 Volume 37 Issue 12 Pages 1081-1085
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Properties, manipulations, preparative methods and typical reactions have been described for the following twelve representative nickel compounds which have been used and/or should be useful as catalysts and/or reagents for synthetic organic reactions : nickel (II) halides, his (acetylacetonato) -nickel (II), nickel peroxide, dichloro (bipyridyl) nickel (II), dihalobis (trialkylphosphine) nickel (II), dichlorobis (triphenylphosphine) nickel (II), dichloro {1, 3-his (diphenylphosphino) propane} nickel (II), trans-chlorophenylbis (triphenylphosphine) nickel (II), tetracarbonylnickel (0), bis (η- 1, 5-cyclooctadienyl) nickel (0), tetrakis (triphenylphosphine) nickel (0), di-μ-bromobis (1-3-η-allyl) dinickel (II).
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  • Organic Syntheses Using Palladium and Ruthenium Compounds
    Shun-Ichi MURAHASHI, Takahiro HOSOKAWA
    1979 Volume 37 Issue 12 Pages 1086-1098
    Published: December 01, 1979
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Recent developments in organic syntheses using palladium and platinum compounds are surveyed. Emphasis is placed on preparation of useful palladium and platinum compounds and their practical applications for organic syntheses.
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  • Taro SAITO
    1979 Volume 37 Issue 12 Pages 1099-1104
    Published: December 01, 1979
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Metal atom syntheses of organometallic compounds are described from the viewpoint, of reactor designs, reaction procedures and interesting examples of the application of the method.Organometallic syntheses using activated metals are also reviewed briefly.
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