• Title/Summary/Keyword: Epoxide ring-opening

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Study on the Optimization of Cationic Ring Opening Polymerization of Silicone-Based Epoxy Monomers for Holographic Photopolymers

  • Kim, Dae-Heum;Chung, Dae-Won
    • Macromolecular Research
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    • v.17 no.9
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    • pp.651-657
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    • 2009
  • This study examined the optimum compositions of binder, photo-acid generator (PAG) and sensitizer for the cationic ring opening polymerization of 1,3-bis[2-(3-{7-oxabicyclo-[4.1.0]heptyl})]-tetramethyldisiloxane in the presence of polydimethylsiloxane with four epoxide moieties as a co-monomer. When diffractive efficiency (DE) values were compared quantitatively to analyze the effect of the binder on holographic photopolymerization, DE was affected by the viscosity of the binders and miscibility with the monomer mixture. Extremely low DE values were observed when the immiscible dimethyl silicone was used as a binder. Therefore, methylphenyl silicone, which is miscible with the monomer mixture, was used as the binder for further studies. The optimal conditions were a binder viscosity between 250 to 390 cP, and contents of the binder, PAG, and sensitizer were 75-125 wt%, > 6 wt% and 0.05 wt% to the total monomer mixture, respectively.

Regiospecific Ring-Opening of Unsymmetrical Epoxides to the Corresponding Less Substituted Alcohols by Newly-Devised Meerwein-Ponndorf-Verley Type Reagents

  • Cha, Jin Soon
    • Journal of Integrative Natural Science
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    • v.5 no.2
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    • pp.91-99
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    • 2012
  • A newly-devised Meerwein-Ponndorf-Verley (MPV) reagents, such as diisobutylacetoxyalanes and diisobutylmethanesulfonylalanes, achieved a clean conversion of unsymmetrical epoxides to the corresponding less substituted alcohols. This review covers the recent developments for such a regiospecific ring-opening reaction of epoxides.

Selective Ring-opening Fluorination of Epoxide: An Efficient Synthesis of 2'-C-Fluoro-2'-C-methyl Carbocyclic Nucleosides

  • Liu, Lian-Jin;Kim, Si-Wouk;Lee, Won-Jae;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.30 no.12
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    • pp.2989-2992
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    • 2009
  • An efficient synthetic route of novel 2′(${\alpha}$)-C-fluoro-2′(${\beta}$)-C-methyl carbocyclic nucleoside analogues is described. The key fluorinated intermediate 7 was prepared from the epoxide intermediate 5 via selective ring-opening of epoxide. Coupling of 7 with nucleosidic bases under the Mitsunobu reactions followed by deprotection afforded the target carbocyclic nucleoside analogues. The synthesized compounds were evaluated as inhibitors of the hepatitis C virus (HCV) in Huh-7 cell line in vitro.

Enantioselective Epoxide Synthesis on the Chiral Salen Catalyst having a Transitional Metal Salt (전이금속염 함유 키랄 살렌 촉매에 의한 광학선택적 에폭사이드의 합성)

  • Guo, Xiao-Feng;Kawthekar, Rahul B.;Kim, Geon-Joong
    • Korean Chemical Engineering Research
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    • v.46 no.4
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    • pp.769-776
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    • 2008
  • The stereoselective synthesis of chiral terminal epoxide is of immense interest due to their utility as versatile starting materials as well as chiral intermediates. In this study, new chiral Co(salen) complexes bearing cobalt(II) chloride, iron(III) chloride and zinc(II) nitrate have been synthesized and characterized. The mass and EXAFS spectra provided the direct evidence of formation of complex. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of terminal epoxides such as styrene oxide and phenylglycidylether by hydrolytic kinetic resolution technology and for the synthesis of glycidyl buthylate. The easily prepared complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ nucleophile, providing enantiomerically enriched terminal epoxides (>99% ee). The newly synthesized chiral salen showed remakablely enhanced reactivity with substantially low loadings. The system described in this work is very efficient for the sinthesis of chiral epoxide and 1,2-diol intermediates.

Efficient Ring Opening Reaction of Epoxides with Oxygen Nucleophiles Catalyzed by Quaternary Onium Salt

  • Kim, Jin Won;Cho, Dae Won;Park, Gyoosoon;Kim, Sung Hong;Ra, Choon Sup
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2286-2290
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    • 2013
  • Ring opening reactions of epoxides with oxygen nucleophiles catalyzed by a variety of quaternary onium salt, such as ammonium or phosphonium salt were explored. The results showed that tetrabutylphosphonium bromide (TBPB) among salts serves as the most efficient catalyst for this process and that expoxide ring opening reactions with a variety of oxygen nucleophiles including carboxyic acid and phenol, promoted using this salt, lead to generate readily purifiable products in excellent yields.