Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Volume 26, Issue 10
Displaying 1-11 of 11 articles from this issue
  • Toshihiko MIGITA, Wataru ANDO
    1968 Volume 26 Issue 10 Pages 835-848
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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  • Shigeo TANIMOTO
    1968 Volume 26 Issue 10 Pages 849-861
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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  • Takeo SAEGUSA, Yoshihiko ITO
    1968 Volume 26 Issue 10 Pages 862-873
    Published: 1968
    Released on J-STAGE: November 13, 2009
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  • Masaji YONEZAWA, Shigenari SUZUKI, Hiro ITO, Hichiro SYODA, Kaoru KIMU ...
    1968 Volume 26 Issue 10 Pages 874-878
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Various methods have been suggested for the preparation of ethyl acrylate.
    In the present study, acrylic acid was esterified using ethyl sulfate to form ethyl acrylate. Thus, a mixture of acrylic acid, ethyl sulfate, and water (1/1. 54/2, mol) mol was heated at 70°C for 2 hrs. The conversion was 88%and the yield was 75% based on the acrylic acid used.
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  • Etsuro OTA, Atsuto ABE, Kenji IWAMOTO
    1968 Volume 26 Issue 10 Pages 879-883
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    In connection with our earlier work on the substitution of phenanthrene, the rearrangement of phenanthrenemonosulfonic acids was investigated.
    Upon treatment of potassium 9-phenanthrenesulfonate with 77% sulfuric acid at 152°C for 5 hrs, a mixture of the 2-and 3-isomers containing a small amount of polysufonates and phenanthrene was obtained. The sulfonation product of phenanthrene containing the 1-sulfonate as obtained with the aid of a SO3-dioxane complex also gave a similar mixture by the same treatment. This indicates that rearrangement also takes place in the 1-sulfonate.
    The products were analyzed by thin layer chromatography on silica gel, developed by a chloroform-carbon tetrachloride mixture, after converting the sulfonic acids into hydroxy azo compounds through the corresponding phenanthrols. The 2-, 3-, and 9-sulfonates were alkali-fused into the corresponding phenanthrols. By coupling with benzenediazonium chloride, they gave the 1-, 4-, and 10-azo compounds. 1- Phenanthrol, however, afforded a mixture of two or three azo compounds.
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  • The Hydrosilane Reduction. I
    Yoichiro NAGAI, Kazuo YAMAZAKI, Isao SHIOJIMA, Hideyuki MATSUMOTO, Set ...
    1968 Volume 26 Issue 10 Pages 884-889
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Chlorine-hydrogen exchange reaction between a chloroalkane and a hydrosilane was found to occur under rather mild conditions in the presence of free radical initiators. A radical chain mechanism involving alternate formations of silyl and alkyl radicals was proposed to explain the reduction reaction. For the reaction of carbon tetrachloride with triethylsilane, azobisisobutyronitrile was somewhat less effective than benzoyl peroxide or di-tert-butyl peroxide.
    The reduction is very selective. Thus, for example, 1, 2-dichloroethane was obtained from 1, 1, 2-trichloroethane as a sole product. Various chloroalkanes could be reduced in a similar manner and their reactivities appeared to be consistent with the respective carbon-chlorine bond dissociation energies.
    The reduction of simple monochloroalkanes is also possible under somewhat drastic conditions.
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  • Takao TOKUMITSU, Iwao OKAMOTO, Takayuki HAYASHI
    1968 Volume 26 Issue 10 Pages 890-898
    Published: 1968
    Released on J-STAGE: January 21, 2010
    JOURNAL FREE ACCESS
    s-Triazine derivatives (5) containing anthraquinonylamino, arylamino. and 2-hyd-roxyethylamino groups were synthesized from cyanuric chloride.
    _??_O-_??_=ONH-_??_RH-C=N-C=N-C=N-C-NHCH2CH2OH (5) -NH-_??_-R'R : H, NHCH3, OCH3, NH-H or OH
    R' : H, COOK COOC2H5
    Thus, it is recommended to condense cyanuric chloride firstly with p-substituted aniline, secondly with monoethanolamine, and lastly with 1-amino-4-R-anthraquinone to obtain the dyes (5).
    The visible absorption peaks of (5) (R=H, OCH3, or OH) shifted to shorter wavelengths from the ones of the corresponding 1-amino-4-R-anthraquinones. (5) (R=OH) showed only one peak as in the case of benzoylated 1-amino-4-anthraquinones. However, the absorption peaks of (5) (R=NHCH3 or NH-H) essentially duplicate the ones of the corresponding 1-amino-4-R-anthraquinones.
    Dyeing affinity of (5) for Nylon and Vinylon was moderate, and for other fibers. poor.
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  • Studies on Heteroaromaticity. XXVI
    Tadashi SASAKI, Masahiko TAKAHASHI
    1968 Volume 26 Issue 10 Pages 899-900
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    N-Methylisatin β-oxime was irradiated with a 100 watt high pressure mercury lamp in methanol at room temperature under nitrogen stream to afford an isomerization product. In contrast, isatin α-oxime remained unchanged under similar reaction conditions.
    N-Acetylisatin dioxime afforded N-acetylindazolone after 10 hrs' irradiation in tetrahydrofuran, though the yield was low.
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  • Studies on Heteroaromaticity. XXVII
    Tadashi SASAKI, Masahiko TAKAHASHI
    1968 Volume 26 Issue 10 Pages 901-902
    Published: 1968
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    N-Methylisatin (2) was treated with a Meerwein reagent, followed by addition of an equivalent amount of hydrazine hydrate to afford an azine (4). The product was confirmed by comparison with a specimen prepared by the known method. (4) was also prepared by treating N-methylisatin β-hydrazone with a Meerwein reagent and then with an equivalent amount of hydrazine hydrate.
    Similarly, an equivalent amount of thiosemicarbazide was added to the reaction mixture of (2) and a Meerwein reagent to give a 1 : 1 adduct. When two equivalent amounts of thiosemicarbazide were used in the above reaction, the product was N-methylisatin β-thiosemicarbazone, as identified with an authentic specimen.
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  • Hikoya HAYATSU
    1968 Volume 26 Issue 10 Pages 903-907
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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  • Hiroo TOMINAGA
    1968 Volume 26 Issue 10 Pages 908-915
    Published: 1968
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
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