• Applied Chemistry for Engineering
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• v.5 no.5
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• pp.843-850
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• 1994

Polyphosphazene-bound Wittig reagents such as $[NP(OC_6H_5)_{1.7}(OC_6H_4P(Ph)_2$=$CHCH_2CH_2CH_3)_{0.3}]_n$ were synthesized by treating $[NP(OC_6H_5)_{1.7}(OC_6H_4Br)_{0.3}]_n$ with n-butyllithium, diphenylchlorophosphine, and n-butyl iodide. Polymeric reactions were carried out according to the reaction conditions with cyclic primers such as [$N_3P_3(OC_6H_5)_5(OC_6H_4P(Ph)_2$)]. The desired alkene and polymer-bound phosphine oxide were prepared successfully by the reaction of polyphosphazene-bound Wittig reagents with benzophenone.

• Polymer(Korea)
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• v.38 no.3
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• pp.386-390
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• 2014

Efficient stitching methods for the synthesis of tripodal Fr$\acute{e}$chet-type dendrimers containing secondary amine as a connector were elaborated. The synthetic strategy involved Staudinger/aza-Wittig reactions (new click reaction) between tripodal tris(azides) and aldehyde-dendrons in toluene in the presence of triphenylphosphine and followed by the reduction of imine intermediates. The tripodal core (1,3,5-tris-(3-azido-propoxy)-benzene) was chosen to serve as the azide functionalities for dendrimer growth. 1,3,5-Tris-(3-azido-propoxy)-benzene was stitched with the aldehyde-functionalized Fr$\acute{e}$chet-type dendrons via Staudinger/aza-Wittig reactions leading to the formation of the corresponding Fr$\acute{e}$chet-type dendrimers in high yields.

• Journal of the Korean Chemical Society
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• v.48 no.1
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• pp.28-32
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• 2004

The condensation reaction of (benzylene)triphenylphosphoranes with carbonyl compounds in supercritical carbon dioxide was examined. Reactions of (benzylene)phosphoranes (ca. 1 mmol) with several benzaldehydes in a supercritical carbon dioxide (80 $^{\circ}C$, 2,000 psi) containing THF entrainer (5%) in a 24 mL reactor proceed smoothly to yield olefination products in fairly good to excellant yields but slower, compared to reactions in a conventional THF solvent. Generally, phosphoranes that are not substituted with a nitro group show more (Z)-selective reactions with aromatic aldehydes under $scCO_2$ condition than in THF. The reaction of (benzylene)triphenylphosphoranes with 4-t-butylcyclohexanone gave the corresponding olefin compounds with a low conversion under both the supercritical carbon dioxide and the organic THF solvent. Our preliminary study showed the Wittig reaction carries out smoothly in supercritical carbon dioxide medium and also a possibile tunability of this reaction pathway by adding a entrainer. The results would be useful for devising a novel process for the environmentally friendly Wittig reaction.

• Applied Chemistry for Engineering
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• v.16 no.6
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• pp.755-759
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• 2005

This study was based on organic electroluminescence display. Especially, DPAVBi, AVBi and DPVBi for the emitting materials were synthesized by Wittig, Wittig-Horner reaction. This reaction was conducted between phosphorous ylide and 4-(diphenylamino)benzaldehyde, 9-anthraldehyde and benzophenone. The structural property of reaction products were analyzed by FT-IR, $^1H-NMR$ spectroscopy and thermal stability, reactivity and PL property were analyzed by melting point, yield and emission spectrum, respectvely. The photoluminescence spectra of a pure DPAVBi, AVBi and DPVBi were observed at approximately 445nm, 484nm and 450nm, respectively. In this study, it was known that DPAVBi, AVBi, DPVBi had a different reaction properties according to stability of ${\alpha}$-position carbonyl group of the aldehyde, ketone.

• Journal of the Korean Chemical Society
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• v.42 no.1
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• pp.69-77
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• 1998

(3S,4S)-1-(t-Butoxycarbonylmethyl)-3-[(S)-1-(t-butyldimethylsilyloxy)ethyl]-4-(2-diazo-2-ethoxycarbonyl-1-oxoethyl)-2-azetidinone (14) was prepared from 4-styryl-2-azetidinone 7b via a sequence of reactions involving N-alkylation with bromoacetate, ozonolysis, oxidation, condensation with magnesium ethyl malonate, and diazo transfer reaction. (3S,4S)-3-[(S)-1-(t-Butyldimethylsilyloxy)ethyl]-4-(3-diazo-3-ethoxycarbonyl1-hydroxypropyl)-2-azetidinone (21) was also prepared from 4-formyl-2-azetidinone 5b via a sequence of reactions involving Wittig reaction, 1,3-dipolar cycloaddition with ethoxycarbonylformonitrile oxide, catalytic hydrogenation, and diazotization. However, the final cyclization of 14 or 21 to 1-hydroxycarbapenem or 1-hydroxycarbapenam by treating with $Rh_2(OAc)_4$ was unsuccessful.

• Journal of the Korean Chemical Society
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• v.45 no.4
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• pp.312-317
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• 2001

7'-Aldehyde-nucleosides analogue (2a, 2c) were synthesized from 6-N-benzoyl-2',3'-O-isopropylideneadenosine and uridine. The condensation of 2 with ethoxycarbonylmethylene Wittig reagent produced the adenosine and uridine analogues containing extended conjugated diene and ethoxycarbonyl group, ethyl-1',5',6',7',8'-pentadeoxy-1'-(adenin-9-yl)-$\beta$-D-ribo-nona-5'(E),7'(E)-dienofuranuronate (4b) and ethyl-1'. 5',6',7',8'-pentadeoxy-1'-(uracil-1-yl)-$\beta$-D-ribo-nona-5'(E),7'-(E)-dienofuranuronate (4c). 9-[8',8'-dibromo-5',6',7',8' -tetradeoxy-$\beta$-D-ribo-octa-5'(E),7'(E)-diene]nucleosides (6b, 6c) were also prepared from 2 with similar method.

• Applied Chemistry for Engineering
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• v.22 no.4
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• pp.348-352
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• 2011

In this research, we have synthesized new pendant-type polyurethane polymers by introducing various chromophores with stilbene derivatives in the side-chain of the polymer backbone. The Stilbene monomers, N,N-bis(2-hydroxyethyl) amino-4'-cyanostilbene, N,N-bis(2-hydroxyethyl)amino-4'-methoxy stilbene, N,N-bis(2-hydroxyethyl)amino-4'-acetylstilbene, and N,N-bis(2-hydroxyethyl) amino stilbene, were synthesized by Wittig reaction. Another stilbene monomer, N,N-bis(2-hydroxyethyl)amino-4'-nitrostilbene, was synthesized by Knoevenagel condensation. By the measurement of UV-Vis absorption and Photoluminescence (PL) spectrum, we found that introduction of the electron-withdrawing group as a substituent shifts both UV-Vis and PL spectra to longer wavelength, and the introduction of the electron-donating group results in blue-shift of the spectrum. In case of polymer with $NO_2$ group as a substituent, PL is quenched.

• Applied Biological Chemistry
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• v.37 no.1
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• pp.25-29
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• 1994

2-methyl-5(S)-hexanolide(1); the major component of pheromonal blend of the male carpenter bee was synthesized via Homer-Emmons reaction from Ethyl(S)-3-hydroxybutyrate(2a) which had been obtained by Baker's Yeast reduction in overall yield 39%.

• Journal of the Korean Wood Science and Technology
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• v.23 no.4
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• pp.98-107
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• 1995

천연물 중 casbene-type diterpenoid의 하나인 crotonitenone의 합성이 시도되었다. 합성 방법으로는 crotonitenone의 각 부분을 먼저 합성하여 이들을 합하는 방법(convergent method)을 적용하였으며, 각 부분이 최종물질에 적합한 sterochemistry를 갖게 하기 위하여 시작물질로는 chiron으로 S-(-)-citronellol과 IS-chrysanthemic acid를 사용하였다. 환구조를 형성하는데 중요한 역할을 할 TBDMS protecting group이 붙은 phosphonium salt(synthon A) 가 고압반응으로부터 고수율 (70%)로 생성되었다. 또한, 중요한 반응으로서 synthon A와 hydroxy lactone(synthon B)과의 Witting reaction이 성공적으로 이루어졌다. 그러나, TBDMS protecting group의 존재하에 이중 치환된 이중결합(disubstituted double bond)과 삼중치환된 것과의 선택적인 환원의 어려움으로 인하여 최종 물질의 합성방법이 재고되었으며 이에 대해 간단히 논하였다.

• Applied Chemistry for Engineering
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• v.29 no.3
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• pp.303-306
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• 2018

Methyl 4-formylbenzoate (MFB), a by-product of the DMT production process, which has been disposed, was used as a starting material for the synthesis of six new fluorescent whitening agent's candidates with 4,4'-di((E)-styryl)-1,1'-biphenyl skeleton attached with an aromatic ester, the same as that of the commercial product family. All candidates were synthesized by the reaction of MFB, and its derivatives with tetraethyl biphenyl-4,4'-diylbis(methylene)diphosphonate using Wittig-Horner reaction. UV spectra for all candidates were recorded and the data were used for calculating the molar absorptivity in order to confirm the usability as a fluorescent whitening agent. All of them showed overall molar extinction coefficients (log ${\varepsilon}$ 4.59~5.00) similar to those of conventional commercial products (log ${\varepsilon}$ 4.85). In particular, compounds 16 and 17 having a dimethoxyphenyl group exhibited a molar extinction coefficient superior to those of conventional commercial products, and thus a field testing for commercialization will be conducted.