• Title/Summary/Keyword: [5+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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    • v.29 no.6
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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.

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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    • v.13 no.1
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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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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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    • v.35 no.5
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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.

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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    • v.31 no.5
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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.

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

  • Shim, Pil-Jong;Kim, Hee-Doo
    • YAKHAK HOEJI
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    • v.41 no.6
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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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Regio- and Diastereoselective 1,3-Dipolar Cycloaddition between Perfluoro-2-methyl-2-pentene and Nitrones: A Facile Approach to Partially-Fluorinated Isoxazolidines

  • Moon, Mi-Eun;Park, Joo-Yeon;Jeong, Eun-Ha;Vajpayee, Vaishali;Kim, Hyun-Uk;Chi, Ki-Whan
    • Bulletin of the Korean Chemical Society
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    • v.31 no.6
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    • pp.1515-1518
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    • 2010
  • Regio- and diastereoselective 1,3-dipolar cycloaddition reactions of nitrones {(Z)-${\alpha}$-phenyl-N-methylnitrone (1a) and (Z)-${\alpha}$-propyl-N-butylnitrone (1b)} with electron-deficient perfluoro-2-methyl-2-pentene (2) lead to novel isoxazolidines {5-fluoro-5-pentafluoroethyl-4,4-bis-trifluoromethyl-2-methyl-3-phenyl-isoxazolidine (3a) and 2-butyl-5-fluoro-5-pentafluoroethyl-4,4-bis-trifluoromethyl-3-propyl-isoxazolidines (3b) respectively} as major constituents. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, GC-MS and NOE measurements, and the absolute structure of 3a was confirmed by X-ray crystallography.

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

  • Kim, Dong-Woo;Kim, Hyeon-Gook;Cho, Deug-Hee
    • Applied Chemistry for Engineering
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    • v.27 no.3
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    • pp.239-244
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    • 2016
  • The catalytic applicability of various ionic liquids immobilized on different silica-supports such as amorphous, SBA, MCM and commercial silica for the cycloaddition of $CO_2$ and epoxides is reviewed in this work. The effects of different structures of supported ionic liquids and silica supports in the synthesis cyclic carbonate by the cycloaddition of $CO_2$ have been remarked. The studies revealed that ionic liquids possessing functional groups or metals exhibited increased catalytic performance towards cyclic carbonate synthesis. Moreover, the reusability of SSIL catalyst and mechanism for the cycloaddition of $CO_2$ were studied.