• Title/Summary/Keyword: Cyclohexene derivatives

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Cycloolefins Oxidation Reaction Catalyzed by Ga(III)-, In(III)- and TI(III)-Porphyrin Derivatives (Ga(III)-, In(III)-, TI(III)-porphyrin 유도체를 촉매제로 한 고리성 올레핀의 산화반응)

  • Na, Hun-Gil
    • Journal of the Korean Applied Science and Technology
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    • v.21 no.1
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    • pp.76-88
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    • 2004
  • The catalytic oxidation reaction of several cycloolefins in $CH_2Cl_2$ have been investigated using non-redox metalloporphyrin(M = Ga(III), In(III) and TI(III) complexes as a catalyst and sodium hypochlorite as a terminal oxidant. Porphyrins were $(p-CH_3O)$TPP, $(p-CH_3)$TPP, TPP, (p-F)TPP, (p-Cl)TPP and $(F_{20})$TPP (TPP=5,10,15,20-tetraphenyl-21H,23H-porphyrin) and olefins were cyclopentene, cyclohexene, cycloheptene and cyclooctene, The substrate conversion yield(%) was investigated according to the radius effect of non-redox metal ion, substituent effect and hindrance effect of metalloporphyrin. The conversion yield of cycloolefin was in the following order : $C_5$ < $C_6$ < $C_7$ = $C_8$.

Alignment of smectic liquid crystals on newly synthesized photo-reactive polyimide with chalcone moiety

  • Song, Dong-Mee;Shin, Dong-Myung;Kim, Jae-Hoon;Kim, Il
    • 한국정보디스플레이학회:학술대회논문집
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    • 2002.08a
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    • pp.479-482
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    • 2002
  • Benzylideneacetophenones are known as chalcones[1]. The chalcone has been known to be a photo-isomerizable and photo-dimerizable chromophore. The chalcone derivatives were prepared by base-catalyzed condensation of aldehydes and acetophenones, which were substituted with various alkyl chains. The synthesized chalcone was introduced into the t-BOC protected diamine through William synthesis reaction. Photocrosslinkable polyimide was prepared via one-step imidization reaction of DOCDA (5-(2,5-dioxotetrahydro furyl}-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride) and the chalcone introduced diamine using isoquinoline (5 wt%) in m-cresol. The polyimide solutions were spin-coated onto the quartz, silicone wafer and glass substrates and the obtained thin films were irradiated obliquely with linearly polarized UV light.

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Study on the Synthsis of Tetramethyldisiloxane Derivatives Containing Silicone Hydride and Epoxy Functionalities at Each End (실리콘 하이드라이드 및 에폭시 관능기를 양 말단에 포함하는 테트라메틸디실록산 치환체의 합성에 관한 연구)

  • Chung, Dae-Won;Kang, Min Ha
    • Applied Chemistry for Engineering
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    • v.18 no.2
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    • pp.116-120
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    • 2007
  • The synthesis of 1-[2-(3-{7-oxabicyclo[4.1.0]heptyl} 1,1,3,3-tetramethyl-disiloxane (Mono), which is a key intermediate for the synthesis of monomers applied for photopolymer systems based on the cationic ring opening polymerization, was studied. Mono was successfully synthesized by the hydrosilylation reaction of 4-vinyl-1-cyclohexene 1,2-epoxide (VCHO) with an excess amount of 1,1,3,3-tetramethyldisiloxane (TMDS) in the presence of a Speier catalyst. The structure and the purity of Mono were characterized by FT-IR, $^1H-NMR$, and $^{29}Si-NMR$. The optimum conditions for the hydrosilyation reaction were found to be 1:4 molar ratio of VCHO to TMDS and 5 ppm of the catalyst at the temperature of $55^{\circ}C$.

A Study for Kinetics and Oxidation Reaction of Substituted Benzyl Alcohols Using Cr(VI)-6-Methylquinoline (Cr(VI)-6-Methylquinoline을 이용한 치환 벤질 알코올류의 산화반응과 속도론에 관한 연구)

  • Park, Young Cho;Kim, Young Sik
    • Applied Chemistry for Engineering
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    • v.26 no.3
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    • pp.372-376
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    • 2015
  • 6-MQCC (Cr(VI)-6-methylquinoline) complex was synthesized by the reaction of 6-methylquinoline with chromium(VI) trioxide in 6 M HCl. The structure was characterized using IR (Infrared Spectroscopy) and ICP (Inductively Coupled Plasma) analysis. The oxidation of benzyl alcohol using 6-MQCC in various solvents showed that the reactivity increased with the increase of the dielectric constant, in descending order of DMF > acetone > chloroform > cyclohexene. In the presence of DMF solvent with acidic catalyst such as sulfuric acid ($H_2SO_4$), 6-MQCC oxidized benzyl alcohol (H) and its derivatives ($p-OCH_3$, $m-CH_3$, $m-OCH_3$, m-Cl, $m-NO_2$) were effectively oxidized. Electron-donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (${\rho}$) was -0.69 (308 K). The observed experimental data was used to rationalize the fact that the hydride ion transfer occurred at the rate-determining step.

Mechanism for the Oxidation Reaction of Alcohols Using Cr(VI)-Pyrazine Complex (크롬(VI)-피라진 착물을 이용한 알코올류의 산화반응과 메카니즘)

  • Park, Young Cho;Kim, Young Sik
    • Applied Chemistry for Engineering
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    • v.27 no.1
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    • pp.110-114
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    • 2016
  • Cr(VI)-pyrazine complex (PZCC) was synthesized by the reaction of pyrazine with chromium (VI) trioxide in 6 M HCl. The structure was characterized using IR spectroscopy and inductively coupled plasma (ICP). The oxidation of benzyl alcohol using PZCC in various solvents showed that the reactivity increased with the increase of the dielectric constant, in the order: N,N'-dimethylform-amide > acetone > chloroform > cyclohexene. In the presence of N,N'-dimethylformamide solvent with an acidic catalyst such as sulfuric acid ($H_2SO_4$ solution), PZCC oxidized benzyl alcohol (H) and its derivatives ($p-OCH_3$, $m-CH_3$, $m-OCH_3$, m-Cl, $m-NO_2$). Electron-donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. Hammett reaction constant (${\rho}$) was -0.70 (308 K). The observed experimental data were used to rationalize the hydride ion transfer in the rate-determining step.

A Study for Mechanism and Oxidation Reaction of Substituted Benzyl Alcohols using Cr(VI)-Heterocyclic Complex[Cr(VI)-2-methylpyrazine] (Cr(VI)-헤테로고리 착물[Cr(VI)-2-methylpyrazine]를 이용한 치환 벤질 알코올류의 산화반응과 메카니즘에 관한 연구)

  • Kim, Young-Sik;Park, Young-Cho
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.14 no.11
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    • pp.6039-6046
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    • 2013
  • Cr(VI)-heterocyclic complex[Cr(VI)-2-methylpyrazine] was synthesized by the reaction between of heterocyclic compound(2-methylpyrazine) and chromium trioxide, and characterized by IR and ICP analysis. The oxidation of benzyl alcohol using Cr(VI)-2-methylpyrazine in various solvents showed that the reactivity increased with the increase of the dielectric constant(${\varepsilon}$), in the order : cyclohexene${\rho}$) was Cr(VI)-2-methylpyrazine= -0.65(308K). The observed experimental data have been ratiolized. The hydride ion transfer causes the prior formation of a chromate ester in the rate-determining step.

Kinetics and Mechanism of the Oxidation of Substituted Benzyl Alcohols by Cr(VI)-Heterocyclic Complex (2,4'-Bipyridinium Chlorochromate) (크롬(VI)-헤테로고리 착물(2,4'-비피리디늄 클로로크로메이트)에 의한 치환 벤질 알코올류의 산화반응에서 속도론과 메카니즘)

  • Park, Young Cho;Kim, Young Sik
    • Applied Chemistry for Engineering
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    • v.25 no.6
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    • pp.648-653
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    • 2014
  • Cr(VI)-heterocyclic complex (2,4'-bipyridinium chlorochromate) was synthesized by the reaction between heterocyclic compound(2,4'-bipyridine) and chromium trioxide, and characterized by IR and ICP analysis. The oxidation of benzyl alcohol using 2,4'-bipyridinium chlorochromate in various solvents showed that the reactivity increased with the increase of the dielectric constant (${\varepsilon}$), in the order : N,N-dimet-hylformamide (DMF) > acetone > chloroform > cyclohexene. In the presence of DMF solvent with acidic catalyst such as hydrochloric acid (HCl solution), 2,4'-bipyridinium chlorochromate oxidized benzyl alcohol (H) and its derivatives (p-$CH_3$, m-Br, m-$NO_2$). Electron-donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (${\rho}$) was -0.67 (303 K). The observed experimental data have been rationalize the proton transfer occurred followed the formation of a chromate ester in the rate-determining step.

Kinetics of the Oxidation of Substituted Benzyl Alcohols using 6-Methylquinolinium Dichromate (6-Methylquinolinium Dichromate를 이용한 치환 벤질 알코올류의 산화반응 속도)

  • Kim, Young-Sik;Park, Young-Cho
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.12 no.12
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    • pp.5990-5996
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    • 2011
  • 6-Methylquinolinium dichromate[$(C_{10}H_9NH)_2Cr_2O_7$] was synthesized by the reaction of 6-methylquinoline with chromium trioxide in $H_2O$, and characterized by IR, ICP. The oxidation of benzyl alcohol using 6-methylquinolinium dichromate in various solvents showed that the reactivity increased with the increase of the dielectric constant(${\varepsilon}$), in the order: cyclohexene < chloroform < acetone < N,N- dimethylformamide. In the presence of hydrochloric acid($H_2SO_4$ solution), 6-methylquinolinium dichromate oxidized benzyl alcohol and its derivatives(p-$OCH_3$, m-$CH_3$, H, m-$OCH_3$, m-Cl, m-$NO_2$) smoothly in DMF. Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant(${\rho}$) was -0.67(303K). The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.

Kinetic Study on the Oxidation Reaction of Substituted Benzyl Alcohols by Cr(VI)-Heterocyclic Complex (2,2'-Bipyridinium Dichromate) (크롬(VI)-헤테로고리 착물(2,2'-Bipyridinium Dichromate)에 의한 치환 벤질 알코올류의 산화반응에 대한 속도론적 연구)

  • Kim, Young Sik;Park, Young Cho
    • Applied Chemistry for Engineering
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    • v.23 no.2
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    • pp.241-246
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    • 2012
  • Cr(VI)-heterocyclic complex (2,2'-bipyridinium dichromate) was synthesized by the reaction between of 2,2'-bipyridine and chromium trioxide in $H_2O$, and characterized by IR and ICP. The oxidation of benzyl alcohol using 2,2'-bipyridinium dichromate in various solvents showed that the reactivity increased with the increase of the dielectric constant, in the order: cyclohexene < chloroform < acetone < N,N-dimethylformamide. In the presence of DMF solvent with acidic catalyst such as $H_2SO_4$ solution, 2,2'-bipyridinium dichromate oxidized the benzyl alcohol and its derivatives (p-$p-OCH_3$, $m-CH_3$, H, $m-OCH_3$, m-Cl, $m-NO_2$). Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant was -0.66 (303 K). The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.