• Title/Summary/Keyword: halogen-halogen exchange

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Highly Convenient and Large Scale Synthesis of 5-chloroindole and its 3-substituted Analogues (5-Chloroindole계 화합물의 Large Scale 합성)

  • Keetha, Laxminarayana;Palle, Sadanandam;Ramanatham, Vinodkumar;Khagga, Mukkanti;Chinnapillai, Rajendiran
    • Journal of the Korean Chemical Society
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    • v.55 no.2
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    • pp.240-242
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    • 2011
  • A large scale and commercially feasible synthesis of 5-chloroindole and its 3-substituted analogues has been described via a halogen - halogen exchange reaction from 5-bromoindole and its derivatives using cuprous chloride and dipolar aprotic solvent N-methyl-2-pyrrolidone in one pot with good yields.

Halogen Exchange Reactions of Cinnamyl Halides

  • Lee, Bon-Su;Lee, Ikchoon
    • Nuclear Engineering and Technology
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    • v.1 no.2
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    • pp.87-90
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    • 1969
  • Halogen exchange reactions of trans-cinnnamyl chloride and bromide with radioactive chloride, bromide and iodide ions in acetone have teen studied. Relative nucleophilicity of halide ions and relative leaving ability have been discussed invoking the principle of HSAB.

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Kinetic Studies on Halogen Exchanges of 2-Naphthylmethyl Chloride

  • Lee, Ikchoon;Yie, Jae-Eui;Kim, Wang-Ki;Lee, Kae-Soo
    • Nuclear Engineering and Technology
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    • v.8 no.2
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    • pp.77-80
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    • 1976
  • The halogen exchange reactions of 2-naphylmethyl chloride have been investigated in actone and acetonitrile. The results were in good accord with PMO theory and HSAB principle.

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Kinetic Studies on Halogen Exchange of Phenacyl Halides

  • Park, Jin-Ha
    • Nuclear Engineering and Technology
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    • v.5 no.1
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    • pp.20-25
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    • 1973
  • Kinetics of halogen exchange reactions of phenacyl halides using radioisotope tracer halide ions in anhydrous acetone have been studied. The reactions wore believed to be SN2 processes and the orders of relative nucleophilicity of halide ions were Cl->I->Br- for the phenacyl chloride and I->Cl->Br- for the phenacyl bromide. These were interpreted in terms of solvation effect of halide ions and HSAB principle.

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Kinetic Studies on Halogen Exchange Reactions of Phenethyl Chloride in Acetone

  • Kim, Shi-Choon;Cheun, Young-Gu;Sakong Yul
    • Nuclear Engineering and Technology
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    • v.7 no.1
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    • pp.25-29
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    • 1975
  • Kinetics of halogen exchange reaction of 1-phenthyl chloride and 2-phenethyl chloride using radioisotopic tracer halide ions in acetone have been studied. The reactions were belived to be S$_{N}$2 processes and the orders of relative nucleophilicity of halide ions were Cl->Br->I-. The reaction rate is slower than that of benzyl chloride. These were interpreted in terms of solvation effect of halide ions and HSAB principle.

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Stereospecific C$_6$-Hydroxyethylation of the Penicillin Nucleus

  • Kim, Wan-Joo;Lee, Gwan-Sun;Shim, Sang-Chul
    • Bulletin of the Korean Chemical Society
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    • v.5 no.5
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    • pp.191-193
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    • 1984
  • 6, 6-Diiodopenicillanic acid was prepared from 6-aminopenicillanic acid using iodine-sodium iodide systems in good yield (60%). Enolates derived from 6-chloro-6-iodo-, 6,6-diiodo-penicillanate have been generated in situ by a metal-halogen exchange process at -$78^{\circ}C$ using methylmangnesium iodide and reacted with acetaldehyde to yield aldols. As the size of remaining halogen atom increases, the proportion of ${\beta}$-face attack was increased. In the case of 6,6-diiodopenicillanate, only ${\beta}$-face attack was observed yielding a single isomer (6S, 8R).

Halogen Exchange Reactions of Benzyl Halides Part Ⅲ-Kinetics of Reactions of Bromide and Iodide Ions with Benzyl Chloride and Bromide in Absolute Acetone (벤질 할라이드의 할로겐 교환반응 (제Ⅲ보) 아세톤 중에서의 염화 및 브롬화 벤질과 브롬화 및 요오드화 이온간의 교환반응)

  • Hangbo Myung-Hwan;Lee Bon-su;Lee Ik Choon
    • Journal of the Korean Chemical Society
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    • v.13 no.2
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    • pp.109-114
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    • 1969
  • Halogen exchange reactions of benzyl halides have been studied in absolute acetone. Rate constants were calculated using an integrated rate expression derived for the reaction involving ion-pair association. The order of nucleophilicity of halide ions in acetone was found to be a reverse of the order in 90% aqueous enthanol solvent. This was interpreted by means of HSAB principle and solvation of halide ions. Net increase in rate of reaction in acetone compared with the rate in protic solvent resulted from large increase in ${\Delta}S^\neq$ rather than decrease in ${\Delta}H^\neq$. The solvation of the transition state also contribute to the net increase in rate.

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Synthesis and Application of Oligo(3-Methylthiothiophene) Using Palladium Catalyst (Palladium 촉매를 이용한 Oligo(3-methylthiothiophene)의 합성과 응용)

  • Park, Sang-Ho;Jung, Moon-Young;Bae, Jin-Young
    • Polymer(Korea)
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    • v.31 no.6
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    • pp.469-473
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    • 2007
  • In this study, oligo(3-methylthiothiophene) was synthesized from thiophene derivative according to the method of reductive coupling using palladium catalyst. For the preparation of monomer, 3-methylthiothiophene was first synthesized through the metal-halogen exchange reaction of 3-bromothiophene with n-butyllithiuim, and the corresponding 2,5-dibromo-3-methylthiothiophene was formed by bromination. Their synthesis and characterization were determined by $^1H-NMR$ and ATR analyses. Thermal stability of the oligothiophene was monitored by thermogravimetric analysis (TGA). Thermal evaporation of the oligo(3-methylthiothiophene) on the substrate was attempted for OTFT applications.