Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Volume 27, Issue 1
Displaying 1-12 of 12 articles from this issue
  • Catalysis and Reaction Mechanism
    Kimio TARAMA
    1969 Volume 27 Issue 1 Pages 1-10
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Download PDF (1364K)
  • Sotaro MIYANO
    1969 Volume 27 Issue 1 Pages 11-22
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Download PDF (1537K)
  • Osamu MANABE
    1969 Volume 27 Issue 1 Pages 23-35
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Download PDF (1878K)
  • Nucleophilic Substitution Reactions of Phenanthrene Derivatives. II
    Etsuro OTA, Kenji IWAMOTO
    1969 Volume 27 Issue 1 Pages 36-40
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Ammonolysis of 9-bromophenanthrene has been studied. Among copper metal and various copper salts tested, cupric acetate proved to be the most effective catalyst. Thus, 9-bromophenanthrene was converted into 9-aminophenanthrene in 73% yield when treated with conc, aqueous ammonia at 180200°C for 510 hrs.
    Phenanthrene and phenanthrazine were commonly identified as by-products. The relationships between the yields and the types or the amounts ot catalysts were also established. When cupric chloride was used, a small amount of 9-chlorophenanthrene was detected as a by-product.
    In the course of distillation in vacuo, a portion of 9-aminophenanthrene was found to be converted into a less volatile compound, presumably 9, 9'-diphenanthrylamine.
    Download PDF (900K)
  • Yukiya TOBE, Masahiko TAKEHARA
    1969 Volume 27 Issue 1 Pages 41-46
    Published: January 01, 1969
    Released on J-STAGE: January 22, 2010
    JOURNAL FREE ACCESS
    Nitration of trichloroethylene using a nitrating mixture with subsequent treatment with alkali hypochlorite appears to serve as an industrial production of chloropicrin. Thus, trichloroethylene is converted into chloropicrin in 82.6% selectivity, representing 71.2% yield.
    The formation of chloronitroacetyl chloride and nitryl chloride upon nitration of trichloroethylene may be visualized as follows. Upon elimination of chlorosulfonic acid from CHClNO2-CCl2OSO3H formed by the simultaneous addition of NO2+ and HSO4- to the starting material, chloronitroacetyl chloride is formed. From the chlorosulfonic acid so formed and free nitric acid, in the presence of sulfuric acid, nitryl chloride is formed.
    The formation of chloropicrin from chloronitroacetyl chloride may be explained as follows. Chloronitroacetyl chloride is converted into the salt of nitrocarboxylic acid in an aqueous alkaline solution. It is then decarboxylated and chlorinated to chloropicrin.
    Download PDF (912K)
  • Yoshio BABA
    1969 Volume 27 Issue 1 Pages 47-50
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    The reaction of free triethylaluminum with carboxylic acid chloride was reported to give a complicated condensation product. In the present study, it has been found that by using a diethyl ether adduct of triethylaluminum, the reaction can be terminated at the stage of monomeric alcohol formation. Attempts to isolate ketones, however, failed to succeed even when sterically hindered acid chloride was used.
    Download PDF (582K)
  • Synthesis of Isocoumarin Derivatives. Part II
    Noboru YAGI, Hiroshi OOMORI, Mitsuo OKAZAKI
    1969 Volume 27 Issue 1 Pages 51-58
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    7-Acetylamino-, benzoylamino- and tosylamino-3-phenylisocarbostyril have been synthesized from the corresponding isocoumarins and aqueous ammonia. In an aqueous solution of methylamine, 7-acetylamino-3-phenylisocoumarin (2a) was hydrolyzed into 4'-acetylaminodesoxybenzoin-2'-carboxylic acid. 7-Acetylamino-N-methyl-3-phenylisocarbostyril was obtained by heating (2a) with methylamine in ethanol in an autoclave at 100°C for 10 hrs. Similarly, N-ethyl, N-n-propyl, and N-n-butyl analogs were prepared. N-Phenyl-isocarbostyril derivative was formed only when (2a) was treated with aniline in the presence of boric acid for 5 hrs at 200210°C. By heating a mixture of (2a) and o-phenylenediamine in the presence of polyphosphoric acid for 2 hrs at 200220°C, 2-amino-6-phenylbenzimidazo [2, 1-a] -isoquinoline (5) was formed. When boric acid was used as a condensing agent, N- (o-aminophenyl) -isocarbostyril derivative, instead of (5), was obtained. 6- Phenylbenzimidazo [2, 1-a] -isoquinoline and acetylamino derivative of (5) were also prepared. Infrared, ultraviolet absorption and fluorescence spectra of these new compounds were measured and discussed.
    Download PDF (986K)
  • Shigeo TANIMOTO, Jiro HORIKAWA, Ryohei ODA
    1969 Volume 27 Issue 1 Pages 59-63
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Four jointed compounds by formaldehyde [N-sulfomethylbenzamide (SMB), p-chloro-N-sulfomethylbenzamide (p-CSM), N-sulfomethyl-p-toluamide (SM-p-T) and N-sulfomethyl-p-anisamide (SM-p-A)] were synthesized, and their transjointing reactions investigated.
    Methylenebis-p-toluamide (MB-p-T), 4, 4'-dichloromethylenebisbenzamide (DCM) and diindolylmethane (DIM) were obtained by the reaction between SMB and each one of p-toluamide, p-chlorobenzamide and indole.
    Methylenebisbenzamide (MBB), DCM, MB-p-T, methylenebis-p-anisamide (MB-p-A), p-chloro-N-phthalimidomethylbenzamide, N-carbazolylmethyl-p-chlorobenzamide and DIM were obtained by the reaction between p-CSM and each one of benzamide, p-chlorobenzamide, p-toluamide, p-anisamide, phthalimide, carbazole, and indole.
    MBB, DCM, MB-p-T, MB-p-A, N-phthalimidomethyl-p-toluamide, N-carbazolylmethyl-p-toluamide and DIM were obtained by the reaction between SM-p-T and each one of benzamide, p-chlorobenzamide, p-toluamide, p-anisamide, phthalimide, carbazole and indole.
    Similarly, MBB, DCM, MB-p-T, MB-p-A, N-phthalimidomethyl-p-anisamide and DIM were obtained by the reaction between SM-p-A and each one of benzamide, p-chlorobenzamide, p-toluamide, p-anisamide, phthalimide and indole, respectively.
    Download PDF (627K)
  • Yasuo YUKI, Toshio KAKURAI, Tatsuya NOGUCHI
    1969 Volume 27 Issue 1 Pages 64-68
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    For the synthesis of new linear polymers containing s-triazine rings in the main chain, the reaction of aliphatic dibiguanides and dicarboxylic acid chlorides has been studied.
    Hexamethylene dibiguanide was treated with isophthaloyl- or terephthaloyl-chloride by the interfacial polycondensation technique. The white powder so formed was soluble in sulfuric acid, formic acid, dimethyl sulfoxide, and partially soluble in o-cresol. It was insoluble in acetone and benzene.
    Structures of the products were discussed based on the IR spectra and TGA curves.
    Download PDF (602K)
  • Yoshio ORITO, Shuichi NIWA
    1969 Volume 27 Issue 1 Pages 69-73
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Several kinds of supported palladium catalysts were prepared and their activities for the hydrogenation of acetone and benzene were investigated.
    For the hydrogenation of acetone, the catalysts containing molybdenum oxide as a promoter were found to be highly active. In case of benzene, satisfactory activity was effected by impregnating the supports with an acidic solution of palladium chloride without any promoter. Palladium on activated carbon catalyst prepared by this method showed an excellent activity when reduced with hydrogen at room temperature. Palladium supported on silica or alumina was very active when calcined at about 450°C in air before reduction. In some cases, an increase in activity was brought about by passing hydrogen chloride over the catalyst at temperatures above 250°C after reduction.
    Download PDF (680K)
  • Tomio TERAI
    1969 Volume 27 Issue 1 Pages 74-82
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Download PDF (1172K)
  • Masuo HAGIWARA
    1969 Volume 27 Issue 1 Pages 86-92
    Published: January 01, 1969
    Released on J-STAGE: November 13, 2009
    JOURNAL FREE ACCESS
    Download PDF (974K)
feedback
Top