• Title/Summary/Keyword: ene-reaction

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Synthesis of Odorants p-Mentha-8-ene-2-one Derivatives by the Reaction of Dihydrocarvone with Formaldehyde (p-Mentha-8-ene-2-one계 향료합성)

  • 유충규;송기춘
    • YAKHAK HOEJI
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    • v.35 no.4
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    • pp.335-340
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    • 1991
  • The synthetic product of 1-hydroxymethyl-p-mentha-8-ene-2-one was afforded by the reaction between dihydrocarvone and formaldehyde. This reaction involves the aldol condensation. The preferential position of formaldehyde is methyl substituted .alpha.-carbon atom where these enols are regiospecifically formed. The hydroxymethylation of dihydrocarvone was also proved to happen regiospecifically in the position of .alpha.-methyl substituted ketone. When 1-hydroxymethyl-p-mentha-8-ene-2-one reacted with LiAIH$_{4}$, 1-hydroxymethyl-p-mentha-8-ene-2$\beta$-ol obtained. 1-Hydroxymethyl-p-mentha-8-ene-2-one reacted with PDC and chromic acid to give 1-formyl-p-mentha-8-ene-2-one and 1-carboxy-p-mentha-8-ene-2-one. When the hydroxymethyl group of 1-hydroxymethyl-p-menta-8-ene-2-one was reducted to methyl group, 1-methyl-p-menta-8-ene-2-one was obtained. Some of these new compound have certain odor. I, II have woody aroma and IV, V have camphory odors. IX has flowery minty odor.

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Synthesis and Lubricant Additive Properties of Succinimidyl-type Compounds (숙신이미드계 화합물의 합성 및 그의 윤활특성)

  • Park, Chan-gu;Kang, Hocheol;Park, Jong-mok;Lee, Byung Min;Kim, Dong-Pyo
    • Applied Chemistry for Engineering
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    • v.17 no.5
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    • pp.498-503
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    • 2006
  • i-(2',5'-Diketotetrahydrofuranyl)octadecenyl acid (OSA), an intermediate for the lubricating oil additive, was prepared by the ene-reaction of oleic acid with maleic anhydride. The reaction progress was monitored by gas chromatography by analyzing the amount of OSA. The series of succinimidyl compounds were synthesized by the reaction of alkyl amines and OSA. As a kind of lubricant additives, demulsibility, anti-wear, and anti-corrosion properties of these succinimidyl compounds were measured. The derivative of octadecylamine which has relatively long-chained alkyl group has showed good properties.

Study on the Curing Properties of Photo-curable Acrylate Resins (광경화성 아크릴 수지의 경화특성에 관한 연구)

  • Kim, Sung-Hyun;Chang, Hyun-Suk;Park, Sun-Hee;Song, Ki-Gook
    • Polymer(Korea)
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    • v.34 no.5
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    • pp.469-473
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    • 2010
  • The curing mechanism and characteristics of UV curable acrylate resins were studied using Photo-DSC, FTIR, and Raman spectroscopy. Effects of chemical structures of acrylate, numbers of functional group, and UV intensity on curing kinetics were investigated with Photo-DSC. FTIR and Raman spectroscopy has been used to understand curing mechanisms and reaction conversion. In order to investigate the effect of oxygen on the photo-curing reaction, the curing process was compared between the acrylate and thiol-ene resins. The reaction conversion was found to be less than 80% for acrylate resins. The photo-curing reaction of the acrylate resin could not proceed to the end because of oxygen which acts as a reaction inhibitor while the thiol-ene resin was hardly affected from oxygen during the curing process.

Synthesis and Properties of Novel Flame-Retardant and Thermally Stable Poly(amideimide)s from N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino Acids and Phosphine Oxide Moiety by Two Different Methods

  • Faghihi, Khalil;Hajibeygi, Mohsen;Shabanian, Meisam
    • Macromolecular Research
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    • v.17 no.10
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    • pp.739-745
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    • 2009
  • N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g were synthesized by the condensation reaction of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride 1 with two equimolars of Lalanine 2a, L-valine 2b, L-leucine 2c, L-isoleucine 2d, L-phenyl alanine 2e, L-2-aminobutyric acid 2f and L-histidine 2g in an acetic acid solution. Seven new poly(amide-imide)s PAIs 5a-g were synthesized through the direct polycondensation reaction of seven chiral N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g with bis(3-amino phenyl) phenyl phosphine oxide 4 by two different methods: direct polycondensation in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride ($CaCl_2$/pyridine (py), and direct polycondensation in a tosyl chloride (TsCl)/pyridine (py)/N,N-dimethylformamide (DMF) system. The polymerization reaction produced a series of flame-retardant and thermally stable poly(amide-imide)s 5a-g with high yield. The resulted polymers were fully characterized by FTIR, $^1H$ NMR spectroscopy, elemental analyses, inherent viscosity, specific rotation and solubility tests. Data obtained by thermal analysis (TGA and DTG) revealed that the good thermal stability of these polymers. These polymers can be potentially utilized in flame retardant thermoplastic materials.

Stereoselective Synthesis of Farnesol (Farnesol의 입체선택적 합성)

  • Dong-Soo Shin
    • Journal of the Korean Chemical Society
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    • v.36 no.4
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    • pp.579-583
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    • 1992
  • Stereoselective synthesis of farnesol, (2E, 6E)-3,7,11-trimethyldodeca-2,6,10-tiren-1-ol(1), was carried out using 5-bromo-2-methylpent-2-ene(2) as a starting material. After conversion of 5-bromo-2-methylpent-2-ene(2) to the corresponding iodide compound, 5-(4-methylpent-3-enyl)-2,3-dihydrofuran(4) was obtained by alkylation of 5-lithio-2,3-dihydrofuran with 5-iodo-2-methylpent-2-ene. Ni(0)-catalyzed coupling reaction of the dihydrofuran 4 with MeMgI was proceeded to give (3E)-4,8-dimethylnona-3,7-dien-1-ol(5) in 72% yield. The resultant homoallylic alcohol 5 was converted to the (5E)-6,10-dimethylundeca-5,9-dien-2-one(8) in 4 steps. Compound 8 was condensed with dimethylmethoxycarbonylmethylphosponate in benzene follwed by $NaBH_4$ reduction in EtOH to yield (2E, 6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol(1). Ni(0)-catalyzed coupling reaction of MeMgI with dihydrofuran 4 was a key step in this synthesis of farnesol(1).

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An Improved Procedure for 2-amino-5-nitro-4,6-diarylcyclohex-1-ene-1,3,3-tricar Bonitriles; Carbonate on Polymer Support as Mild and Reusable Catalyst

  • Prasanna, T.S.R.;Raju, K. Mohana
    • Journal of the Korean Chemical Society
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    • v.55 no.5
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    • pp.808-811
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    • 2011
  • A new catalytic system has been developed in the synthesis of 2-amino-5-nitro-4,6-diarylcyclohex-1-ene-1,3,3-tricarbonitriles using carbonate on polymer support (Amberlyst A-26 $NaCO_3{^-}$). Short reaction time, simplicity of isolation, safe catalyst and high yields of product are the features.

Synthesis of methyl 5-methylbicyclo (2.2-1)hept-2-ene-5- carboxylate via Diels-Alder Reaction (Diels-Alder 반응을 이용한 methyl 5-methylbicyclo(2-2.1)hept-2-ene-5-carboxylate의 합성)

  • Lee Yoon-Bae;Sung Si-Chang;Shin Eun-Jung;Ha Hong-Sik;Park Chan-Heung
    • Proceedings of the KAIS Fall Conference
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    • 2004.11a
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    • pp.265-268
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    • 2004
  • Methyl methacrlate와 cyclopentadiene을 반응하여 Methyl 5-methylbicyclo(2.2.1)hept-2-ene-5-carboxylate(MMBHC)를 합성코자 하였다. 합성된 MMBHC의 온도, solvent 변화와 촉매($AlCl_3$)의 사용 유무에 따른 endo, exe의 비율을 관찰하였다. 온도가 낮은 경우 온도가 높은 쪽 보다 endo 비율이 높았고 촉매($AlCl_3$)를 사용하였을 때(약 endo : exo = 63 : 37) 촉매를 사용하지 않은 반응(endo : exe = 34 : 66)보다 endo의 비율이 높았다. methyl acrylate를 사용한 경우 같은 조건에서 endo : exe의 비율이 93.5 : 6.5로 MMA를 사용한 경우보다 endo의 비율은 좋았다. 온도가 높은 경우 수율은 좋았지만 exe의 비율이 높았고 solvent에 따라 endo, exe의 선택도는 큰 차이를 보이지 않음을 알 수 있었다.

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Synthesis and Properties of Oligomers Containing 3-Triethylsilyl-1-silacyclopent-3-ene and Borane Derivatives via Polyaddition Reaction

  • Lee, Jung-Hwan;Park, Young-Tae
    • Bulletin of the Korean Chemical Society
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    • v.25 no.6
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    • pp.889-894
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    • 2004
  • Polyaddition reactions of 1,1-diethynyl-3-triethylsilyl-1-silacyclopent-3-ene with several organoborane derivatives have afforded the oligomeric materials containing organosilacyclic group and organoboron moiety along the oligomer main chains. All of these materials are soluble in THF as well as chloroform, and their molecular weights are in the range of 1,990/1,190-21,950/7,050 ($M_w/M_n$) with the polydispersity indexes of 1.67-3.43. The prepared oligomers are characterized by several spectroscopic methods such as $^1H,\;^{13}C, \;^{29}Si,\;^{11}B$ NMR and FTIR spectra along with elemental analysis. FTIR spectra of all the oligomers show that the new strong C=C stretching frequencies appear at 1599-1712 $cm^{-1}$, in particular. The UV-vis absorption spectra of the materials in THF solution exhibit the strong absorption bands at the ${\lambda}_{max}$ of 268-275 nm. The oligomeric materials show that the strong excitation peaks appear at the ${\lambda}_{max}$ of 255-279 nm and the strong fluorescence emission bands at the ${\lambda}_{max}$ of 306-370 nm. All the spectroscopic data suggest that the obtained materials contain both the organoboron ${\pi}$-conjugation moiety of C=C-B-C=C and the organosilacyclic group of 3-triethylsilyl-1-silacyclopent-3-ene along the oligomer main chains. The oligomers are thermally stable up to 162-200 $^{\circ}C$ under nitrogen.