• Bulletin of the Korean Chemical Society
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• 제21권8호
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• pp.761-762
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• 2000

• Bulletin of the Korean Chemical Society
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• 제31권5호
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• pp.1305-1308
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• 2010

Regioselective perfluorinated isoxazolidine (5 and 7), isoxazoline (9) and 1,2-addition products (6 and 8) having a long alkyl chain functionality have been prepared by 1,3-dipolar cycloaddition between a 1,3-dipole (NH-nitrone or nitrile oxide) and dipolarophile (perfluoro-2-methyl-2-pentene or styrene), respectively. Interestingly, unusual extended conjugated form of isoxazoline adduct (10) was obtained by dehydrofluorinated reaction from the corresponding perfluorinated isoxazoline adduct (9) which was derived from cycloadition between the perfluorinated long alkyl nitrile oxide 1,3-diplole and styrene olefin. This synthetic methodology of heterocyclic compound having a long alkyl chain functionality is useful for the designing of synthetic strategy and potential self-assembled monolayers (SAM) application. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and MASS analysis.

• Bulletin of the Korean Chemical Society
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• 제17권7호
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• pp.595-599
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• 1996

1,3-Dipolar cyclization of various nitrile oxides with 3(2H)- and 2(5H)-furanones regioselectively furnished the corresponding syn-addition products of 3-oxotetrahydro-furano[4,5-d]isoxazolines and 2-oxotetrahydrofurano[3,4-d]isoxazolines.

• Korean Chemical Engineering Research
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• 제54권4호
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• pp.574-581
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• 2016

본 연구에서는 탄소나노튜브에 다양한 아미노산과 알데히드의 1,3-dipolar cycloaddition 반응을 통해 pyrrolidine 고리를 도입하여 기능화된 탄소나노튜브를 합성하였다. 기능화된 탄소나노튜브에 메탈로센 촉매를 담지하였고 in-situ 에틸렌 중합을 통해 탄소나노튜브/폴리에틸렌 복합체를 합성하였다. 글리신과 벤즈알데히드로 기능화된 탄소나노튜브(Gly+BA-CNT)에 담지된 메탈로센 촉매는 낮은 지르코늄 함량에도 불구하고 높은 지르코늄 함량을 나타내는 N-benzyloxycarbonylglycine과 파라포름알데히드로 기능화된 탄소나노튜브(Z-Gly+PFA-CNT)에 담지된 촉매와 유사한 중합 활성을 보였다. N-Benzyloxycarbonylglycine과 파라포름알데히드로 기능화된 탄소나노튜브(Z-Gly+PFA-CNT)에 담지된 메탈로센 촉매의 경우 촉매 활성점의 분포가 조밀하여 에틸렌 중합 시 활성점으로 에틸렌 모노머와 공촉매 MAO가 확산하는데 입체적 방해를 주기 때문이다. 균일계 메탈로센 촉매로 생성된 폴리에틸렌과 비교하여 표면 기능화된 탄소나노튜브에 메탈로센을 담지한 촉매로 생성된 CNT/PE 복합체는 높은 분해 개시 온도($T_{onset}$)와 최대 중량 감소 온도($T_{max}$)를 가진다. 이는 pyrrolidine 고리가 기능화된 CNT는 PE 매트릭스 내에 균일하게 분산되고 CNT와 고분자 간의 강한 상호작용으로 인해 열적 안정성이 향상된 것으로 판단된다.

• Bulletin of the Korean Chemical Society
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• 제31권5호
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• pp.1172-1176
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• 2010

Regioselective perfluorinated [3+2] cycloadducts and 1,2-adducts have been prepared by 1,3-dipolar cycloaddition between benzaldoxime NH-nitrone and perfluorinated alkene, perfluoro-2-methyl-2-pentene. Although the cycloaddition reaction is carried out at room temperature, the corresponding perfluorinated compounds are effectively produced in a high yield. In particular, the methoxy-substituted adducts (4 and 7a) show the self-assembled structure by intermolecular interactions. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and the absolute structure of perfluorinated adducts was confirmed by X-ray crystallography.

• Bulletin of the Korean Chemical Society
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• 제33권1호
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• pp.137-142
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• 2012

The convergent synthetic strategy for the emissive dendrimers having the chromophore at core via the coppercatalyzed 1,3-dipolar cycloaddition reaction between alkyne and azide was described. 2,7-Diazido-9,9-dioctyl-9H-fluorene, designed to serve as the core in dendrimer, was stitched with the alkyne-functionalized Frechettype and PAMAM dendrons by the click chemistry leading to the formation of the corresponding fluorescent dendrimers in high yields. The preliminary photoluminescence studies indicated that 2,7-diazido-9,9-dioctyl-9H-fluorene showed no fluorescence due to the quenching effect from the electron-rich ${\alpha}$-nitrogen of the azido group but the dendrimers fluoresced due to the elimination of the quenching through the formation of the triazole ring.

• 대한화학회지
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• 제43권3호
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• pp.302-306
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• 1999

Quinoxaline 4-oxide 10을 2-chloroacrylonitrile과 반응시켜 1,3-쌍극성 고리화 첨가반응으로 2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline류 11a, b를 합성하였고, 이들을 2,3,4,6-tetrahydro-1H-1,2-diazepino-[3,4-b]quinoxaline 12로 변환시켰다. 그리고 ??嵐?11a를 아세트산/물 용매에서 SeO2와 반응시켜서 고리변환에 의해 1,4-dihydro-4-oxopyridazino[3,4-b]quinoxaline 13을 합성하였다.

• Bulletin of the Korean Chemical Society
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• 제31권3호
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• pp.694-696
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• 2010

• 대한화학회지
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• 제45권4호
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• pp.318-324
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• 2001

6-Chloro-2-hydrazinoquinoxaline(4) 또는 6-chloro-hydrazinoquinoxaline 4-oxide(7)를 alkyl(ethoxymethylene)cyanoacetate류와 반응시켜 prazolylquinoxaline류(5,8)를 합성하였다. 그리고 화합물 8을 dimethyl acethylenedicarboxylate와 반응시켜 1,3-쌍극성 고 리와 첨가반응과 고리변환에 의하여 pyrazolylpyrrolo[1,2-a]quinoxaline류(9)를 합성하였다.

• Bulletin of the Korean Chemical Society
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• 제35권5호
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• pp.1403-1408
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• 2014

The cycloaddition reactions of the N-heterocyclic carbene boryl azide with methyl acrylate, butenone, and hexafluoropropene have been investigated theoretically. Solvent effects on these reactions have been explored by calculation that included a polarizable continuum model (PCM) for the solvent (C6H6). The title reaction could produce 4- and 5-substituted 1,2,3-triazolines, respectively. The reaction systems have the higher chemical reactivity with the low barriers and could be favored. Yet the smaller differences have been found to occur in energetics, and the cycloaddition reactions occur for s-trans conformations over s-cis conformations. The calculations indicated that the cycloaddition reaction of the alkenes have certain regioselectivity.