• 제목/요약/키워드: [2+2+2] Cycloaddition

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Control over [2+2+2] and Carbonylative [4+2] Cycloaddition by CO Pressure in Co-Catalyzed Cycloaddition between Internal Diynes and Cyclopentadiene

  • Kim, Do-Han;Chung, Young-Keun;Han, Jin-Wook
    • Bulletin of the Korean Chemical Society
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    • 제29권6호
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    • pp.1224-1228
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    • 2008
  • The reaction of internal diynes and cyclopentadiene in the presence of 5 mol % of cobalt catalysts proceeded under 5 atm of carbon monoxide pressure to give a high yield of the corresponding [2+2+2] cycloaddition product. By lowering carbon monoxide pressure from 30 atm to 5atm, cyclopentadiene can be used as a dienophile in the cobalt carbonyl-catalyzed [2+2+2] cycloaddition reaction between internal diynes and cyclopentadiene.

입체선택적인 분자내 [2+2] 환화반응을 이용한 광학활성 Bicyclo[4.2.0.]octanone의 합성 (Synthesis of The Optically Active Bicyclo [4.2.0. ] octanone by Stereoselective Intramolecular [2+2] Cycloaddition)

  • 심필종;김희두
    • 약학회지
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    • 제41권6호
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    • pp.714-717
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    • 1997
  • Stereoselective synthesis of the optically active bicyclo [4.2.0] octanone 5 was accomplished using intramolecular olefin-keteniminium salt[2+2]cycloaddition of the amide 4 as a key step. This important chiral synthon was prepared starting from readily available L-glutamic acid via an efficient 8-step sequence.

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Cycloadditiona reaction of 5-(2-thienyl)methylene derivatives of thiazolidinone-4-thiones and their antimicrobial activities

  • Ead, Hamed A.;Metwalli, Nadia H.;Morsi, Nagwa M.
    • Archives of Pharmacal Research
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    • 제13권1호
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    • pp.5-8
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    • 1990
  • The cycloaddition of the newely synthesized 5-(2-thienyl)methylene derivatives of thiazolidinone-4-thiones, 2a-c to acrylonitrile (3a), ethylacrylate (3b), N-phenylmaleimide (6) and dimethyl fumarate (8) has been evaluated. Under thermal reaction conditions [4 +2] cycloaddition proceeds with complete site and regioselectivity to yield the cycloadduct, 4, 5, 7 and 9, respectively. The antimicrobial activities of some of the new products were tested.

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Regioselective 1,3-Dipolar Cycloaddition and 1,2-Addition between Benzaldoxime NH-nitrone and Perfluoro-2-methyl-2-pentene

  • Lee, Chan-Woo;Park, Joo-Yuen;Kim, Hyun-Uk;Chi, Ki-Whan
    • 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.

CO2 부가반응에 적용된 Silica 담지 이온성 액체 촉매 (Application of Silica-supported Ionic Liquid Catalysts to Cycloaddition of CO2)

  • 김동우;김현국;조득희
    • 공업화학
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    • 제27권3호
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    • pp.239-244
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    • 2016
  • 본 총설에서는 $CO_2$와 에폭시 화합물의 부가반응에서 무정형, SBA, MCM 또는 상업적으로 쉽게 이용 가능한 다양한 silica 지지체에 담지된 이온성 액체의 촉매적 적용가능성에 대하여 검토하였다. $CO_2$ 부가반응에 의한 5원환 카보네이트의 합성에 대하여 담지된 이온성 액체의 구조적인 영향과 silica 지지체의 종류에 따른 촉매 활성을 검토한 바, 관능기 또는 금속을 보유한 이온성 액체인 경우에 촉매 성능이 개선됨을 알 수 있었다. 또한 silica에 담지된 이온성 액체(SSIL) 촉매의 재사용성과 반응메커니즘을 조사하여 제시하였다.

Density Functional Study on [3+2]-Dipolar Cycloaddition Reaction of the N-heterocyclic Carbene Boryl Azide with Olefins

  • Zhang, Xing-Hui;Wang, Ke-Tai;Niu, Teng;Li, Shan-Shan
    • 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.