Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Spotlight Archives
Volume 18, Issue 3
Displaying 1-11 of 11 articles from this issue
  • [in Japanese], [in Japanese]
    1960Volume 18Issue 3 Pages 131-134
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
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  • Masamiti KATAYAMA
    1960Volume 18Issue 3 Pages 135-145
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
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  • Naoki INAMOTO, Toshihiko MIGITA
    1960Volume 18Issue 3 Pages 146-166
    Published: 1960
    Released on J-STAGE: October 20, 2010
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  • Kiyoshige HAYASHI
    1960Volume 18Issue 3 Pages 167-174
    Published: 1960
    Released on J-STAGE: October 20, 2010
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  • Koji MATSUI, Ichiji SAKAMOTO
    1960Volume 18Issue 3 Pages 175-183
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
    Hydrolysis of cyanuric chloride (1) in NaHCO3, Na2CO3, etc. gives a sodium salt of 2, 4-dichloro-6-hydroxy-s-triazine (2), while its hydrolysis with NaOH at low temperature-gives the sodium salt of (2) and that with an excess of NaOH at room temperature gives a sodium salt of 2-chloro-4, 6-dihydroxy-s-triazine (3); the Na salt of (2) and (3), respectively, can be obtained in a crystalline form, and crystalline (3) as a free acid is obtained.
    (2) and (3) are stable in alkaline reaction but unstable in acidic reaction and easily decomposed to give cyanuric acid.(2) and (3) react with aniline and give their corresponding anilino derivatives.By application of their differenceof solubilities in alkali, separation and determination of them are possible. Also, treating of (2) with methanolic-NaOH gives 0-dimethylcyanuric acid. Contrary to this stepwise proceeding of the whole reaction system by alkali hydrolysis, the acid hydrolysis of (1) is slow and it does not proceed stepwise as a whole reaction system due to rapid decompositon of intermediates (2) and (3).
    Stability of (2) and (3) in alkaline reaction may be attributed to the formation of their salts which can be present as anions and this may have the great deactivation effect on the residual chlorine atom.
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  • Reaction of 2, 4-dichloro-S-arylamino-S-triazines with Aniline
    Kohji MATSUI, Kikuyo HAGIWARA, Yoshinobu SOEDA
    1960Volume 18Issue 3 Pages 184-189
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
    In order to clarify the effect of NHR (R=aryl or alkyl group) on the reactivity of active chlorine atom in chloro-s-triazine derivatives, reaction between (A) type chloro-s-triazine, N: CCl. N: CCl. N: CNHR, (A) and aniline has been investigated. A comparison of reaction velocity indicated that the reactivity of (A) and aniline was in the order of -NHC6H4Cl-m>-NHC6H4Cl-p>-NHC6H4OCH3-m>-NHC6H5>-NHC6H4CH3-m>-NHC6H4CH3-p>-NHC6H4OCH3-p=-NHC6H4OC2H5-p, and-NH2>-NHCH3>-NHC2H5=-NHC4H9-n. The effect of X in -NH-X type compounds as well as -O-X was mainly due to its polar effect and this was assumed to be transmitted to s-triazine nucleus through the nitrogen atom.When the X has electron attractive property, the reaction proceed easier, and when he X has electron donating property more difficult.
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  • Role of NH4Cl, CuCl, CuCN and HCl in the Catalyst pretreated with Hydrocyanic acid
    Masaru MASUI
    1960Volume 18Issue 3 Pages 190-197
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
    The effects of change in concentration of NH4C1, CuCl, and HCl in CuC1-NH4C1 catalyst pretreated with HCN on the loss of HCN by evolution, thevelocity of formation of acrylonitrile (AN) and an induction period for formationof AN have been investigated.
    An increase in concentration of NH4Cl in Newland's catalyst accelerated thevelocity of evolution of HCN and the induction period for formation of AN wasgradually increased. Although the velocity of formation of AN was increasedup to a certain concentration of NH4Cl, it decreased gradually thereafter. A peakfor formation of AN was appeared by the presence of an equimolar mixture of NH4Cl and CuCl after passing through the induction period. Also, NH4Cl in thepresence of CuCN had no direct relation in the synthetic reaction of AN atany stage of reaction.
    There was no parallelism between the velocity of lossof HCN by evolution and the velocity of formation of AN.
    An increase in concentration of CuCl caused the loss of HCN by evolutionin an inversely related way and this was inversely relatad to the reaction of NH4Cl. The induction period for AN formation was shortened in such a way asinversely related to the concentration of CuCl, but the velocity of formationof AN was increased up to a certain cencentration of CuCl and became constantthereafter. An increase in concentration of HCl caused an increase in the loss of HCN by evolution and this was accompanied with an increase in the velocity off ormation of AN as well as an increase in induction period for its formationsimilar to that of NH4Cl but it showed no peak in the formation of AN asshown by NH4Cl.
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  • Structure of Ciba Red R
    Yasuo YAMAZAKI, Toichiro ISHII, Minoru ISHIBASHI, Ichiro KUBO
    1960Volume 18Issue 3 Pages 198-202
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
    It is known that Ciba Red R, obtainable from bromination of Ciba Scarlet G, is 5-or 6-bromo-2-acenaphthene-2′-thionaphtheneindigo but the position of bromine has been remained unknown. In order to confirm the structure of Ciba Red R, thionaphthene quinone-2-(p-dimethylamino) anil is condensed with 5-bromo and 6-bromo-l-acenaphthenone, respectively, to give 5-and 6-bromo, analog of Ciba Scarlet G.
    The result indicated that the structure of Ciba Red R is 5-broma-2-acenaphthene-2′-thionaphtheneindigo.
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  • Synthesis of Benzanthrone-peri-dicarboxylic acid N-phenylimides
    Yasuo YAMAZAKI
    1960Volume 18Issue 3 Pages 203-205
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
    Methods of syntheses of benzanthrone-peri-dicarboxylic acid-N-phenylimides (4) have been comparatively examined.
    The results indicated that the processes of 4-benzoylnaphthalic anhydride (1)→benzanthrone-peri-dicarboxylic anhydride (3)→(4) are rational.
    A series of (4) thus synthesized were tested for dyeing quality of cotton andvinylon but the dyeing was not so good. Also, stability towards the sunlight wasinferior for practical application.
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  • Katsumi HAYASHI
    1960Volume 18Issue 3 Pages 206-214
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
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  • Tsuneo SAGO
    1960Volume 18Issue 3 Pages 215-220
    Published: 1960
    Released on J-STAGE: October 20, 2010
    JOURNAL FREE ACCESS
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