• Title/Summary/Keyword: Diazo compounds

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Efficient Synthesis of Spirobarbiturates and Spirothiobarbiturates Bearing Cyclopropane Rings by Rhodium(II)-Catalyzed Reactions of Cyclic Diazo Compounds

  • Wang, Xue;Lee, Yong Rok
    • Bulletin of the Korean Chemical Society
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    • v.34 no.6
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    • pp.1735-1740
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    • 2013
  • Rhodium(II)-catalyzed reactions of cyclic diazo compounds derived from barbituric acid and thiobarbituric acid with a variety of styrene moieties were examined. These reactions provide rapid synthetic routes to the preparations of spirobarbiturates and spirothiobarbiturates bearing cyclopropane rings.

Reactivity and Mechanism for Aryl Carbenic Anion Radicals

  • Sung, Dae-Dong;Uhm, Tae-Seop;Lee, Jong-Pal;Ryu, Zoon-Ha;Kim, Hyung-Tae
    • Bulletin of the Korean Chemical Society
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    • v.14 no.2
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    • pp.183-187
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    • 1993
  • Aryl carbenic anion radicals have been generated from the corresponding alkoxy-aryl diazo compounds by unimolecular decomposition reaction in various electrolyte/solvent systems. The electrochemical reductions of alkoxy-aryl diazo compounds in the electrolyte/solvent system are shown to initially be a one-electron process which affords the corresponding anion radicals. The unimolecular loss of nitrogen is favored at the propagation step and accelerated by the oxygen and carbon atoms of alkoxy group adjacent to the diazo function. The structure of the carbene anion radical in the termination is considered to be a resonance hybrid.

Structure and Reactivity in the Reaction of Diazoindanes and Diazoindanones with Triphenylphosphine : The Formation of Mono-, and Bisphosphazines and Hydrazone-Compounds

  • 성대동;강동효;류준하
    • Bulletin of the Korean Chemical Society
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    • v.18 no.9
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    • pp.945-952
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    • 1997
  • The reactions of diazoindanes and diazoindanones with triphenylphosphine have been studied in acetonitrile. The diazoindanes and diazoindanones react with triphenylphosphazine. The reaction of 1,3-bis(diazo)indan-2-one with a tenfold excess of triphenylphosphine in dry acetonitrile gave the 1,3-bis(phosphazino)indan-2-one, however in acetonitrile containing below of 1% water, the 1,3-bis(hydrazono)indan-2-one was produced by hydrolysis. The phosphazine compound could be easily converted into bishydrazone by recrystallization, due to small amounts of water in the solvent. The reactivity of triphenylphosphine toward diazoindanes and diazoindanones depends on the structrue of the diazo compounds.

1,2-Ferrocenedilazaphosphinines 3:A New Class fo Planar Chiral Ligands for Cu-Catalyzed Cyclopropanation

  • Paek, Seung-Hwan;Co, Thanh Thien;Lee, Dong-Ho;Park, Yu-Chul;Kim, Tae-Jeong
    • Bulletin of the Korean Chemical Society
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    • v.23 no.12
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    • pp.1702-1708
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    • 2002
  • The synthesis and catalytic application of a new class of a new class of planar chiral ferrocenes, 1,2-ferrocenediylazaphosphinines (1 and 2) are described. They are powerful ligands for the copper(I)-catalyzed asymmetric cyclopropanation of a range of alkenes with diazo esters to exhibit an exceptionally high degree of diastereoselectivity(~100% de) in favor of trans isomers, regardless the structure of the olefins and the diazo compounds. Comparative studies between 1 and 2 reveal that the former works better in terms of diastereocontrol. In contrast, however, enantioselectivity is low with both 1 and 2 as a whole although, in certain cases with a proper combination of the olefin and the diazo ester, high optical yields (up to 100% ee) can be achieved. Other reaction parameters such as the reaction temperature and the structure of the ligand do exhibit some influence, although infinitestimal, on both chemical and optical yields.

Analysis of dye components using MECC and ion-pairing chromatography (MECC법과 Ion-Pairing 크로마토그래피법을 이용한 염료성분의 분석)

  • Jeong, Hyuk
    • Analytical Science and Technology
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    • v.19 no.1
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    • pp.31-38
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    • 2006
  • Micellar electrokinetic capillary chromatography(MECC) and HPLC with ion-pairing mechanism were applied for the separation of the well known environmental wastes from dye industry. These compounds include H-acid, J-acid, ${\gamma}$-acid, orthanilic acid, sulfanilic acid and 2-naphthylamine-1,5-disulfonic acid, and are known to be the diazo components of the azo dye. MECC method was also applied to separate few acid dyes including Acid Orange 7, Acid Orange 5 and Acid Blue 92 and direct dye such as Direct Red 80. Informations about the diazo components of any azo dye could be obtained by comparison of electropherogram of the reduction solution of a given dye with those obtained from standard materials such as H-acid, J-acid, ${\gamma}$-acid, orthanilic acid, sulfanilic acid and 2-naphthylamine-1,5-disulfonic acid. It has been concluded that MECC and HPLC with ion-pairing mechanism could be successfully applied for the analysis of unknown dyes and their diazo components.

Fe(HSO4)3 as an Efficient Catalyst for Diazotization and Diazo Coupling Reactions

  • Rahimizadeh, Mohammad;Eshghi, Hossein;Shiri, Ali;Ghadamyari, Zohreh;Matin, Maryam M.;Oroojalian, Fatemeh;Pordeli, Parvaneh
    • Journal of the Korean Chemical Society
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    • v.56 no.6
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    • pp.716-719
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    • 2012
  • Diazo coupling reactions of aromatic amines with 2-naphthol in a green, efficient and easy procedure is described. Ferric hydrogensulfate catalyses this reaction in water at room temperature and short reaction time with high yields. The antibacterial activities of the synthesized compounds against four pathogenic bacteria are also investigated.

Direct Coloration using Self-assembly Fabrication Method on PET Fibers - Surface diazo coupling reaction -

  • Kim, Byung-Soon;Son, Young-A
    • Textile Coloration and Finishing
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    • v.19 no.5
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    • pp.37-40
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    • 2007
  • The electrostatic layer-by-layer technique provides a convenient way to control the construction of ultrathin films at nano-scale ranges and can be easily obtained. It can be also applicable to fiber substrate with dye compounds. We have fabricated multilayer dye films using diazonium resin and three couplers, which are prepared by self-assembly approach. This method is based on layer-by-layer deposition using electrostatic attraction between oppositely charged ions. Beside, the diazo coupling reaction proceeded to form azo dye layer on the PET fibers the same time. The corresponding results of the multilayer films have been discussed on the level of color strength (K/S).