• Title/Summary/Keyword: [2+2] Cycloaddition

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Synthesis of Oligoquinoline Dendronized Fullerenes for Potential Use in Organic Photovoltaic Devices

  • Kwon, Tae-Woo;Jenekhe, Samson A.
    • Bulletin of the Korean Chemical Society
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    • v.33 no.8
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    • pp.2703-2706
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    • 2012
  • New C60 fullerenes derivatives [G1]-C60 (1) and [G2]-C60 (2) comprising of phenylenevinylene bridges and phenylquinoline peripheral surface groups were synthesized by 1,3-dipolar cycloaddition reaction of fullerene C60 with azomethine ylide in situ generated from [Gx]-CHO dendrons (x = 1 and 2) and sarcosine.

A Model Study toward the Synthesis of Xestoquinone and Halenaquinone

  • Ahn, Chan-Mug;Woo, Ho-Bum
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.240.2-240.2
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    • 2003
  • A strategy for synthesis of the furan-fused tetracyclic core of xestoquinone and halenaquinone was explored through a model study. Methyl 8-oxo-4-methyl-4-phenyl-2,7-nonadiynoate was prepared from hydratroponitrile and 3-butyn-1-ol as starting materials. The intramolecular cycloaddition of this intermediate as a key step will be involved.

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Rhodium(III)-mediated cycloaddition reactions of alkynes

  • 한원석;이순원
    • Proceedings of the Korea Crystallographic Association Conference
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    • 2002.11a
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    • pp.30-30
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    • 2002
  • Heating [Cp*Rh(η²-NO₃)(OTf) (1) and PhC≡CPh in EtOH for 3 h gave a η⁴-cyclobutadienerhodium complex, [Cp*Rh(η⁴-C₄Ph₄)] (2). Complex 1 reacted with HC=CPh in acetone at room temperature for 3 h to give a (η⁴-cyclobutadiene)-rhodium complex, [Cp*Rh(η⁴-C₄HPhC=CPh)] (3). Whereas, the reactions of 1 with HC=CCH₂Cl in acetone at room temperature for 3 h gave the triply halide-bridged dinuclear rhodium complex, [Cp*Rh(μ₂-Cl)₃RhCp*](OTf) (4). Complexes 2-4 have been structurally characterized by X-ray diffraction.

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Photoreaction of 8-Methoxypsoralen with Thymine

  • Shim, Sang-Chul;Kim, Yong-Zu
    • Bulletin of the Korean Chemical Society
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    • v.4 no.2
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    • pp.95-99
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    • 1983
  • Photoreaction of 8-methoxypsoralen (8-MOP) with thymine (${\ge}$ 300 nm) was carried out in the dioxane-water frozen state. One major and two minor monoaddition products between 8-MOP and thymine were isolated by various chromatographic methods. Major monoadduct was characterized to be a C4 cycloaddition product formed between 5,6-double bond of thymine and 3,4-double bond of 8-MOP with cis-anti stereochemistry. Two minor adducts were proved to be stereoisomers of this major adduct.

Lewis Acid-Catalyzed Reactions of Anthrone: Preference for Cycloaddition Reaction over Conjugate Addition Depending on the Functionality of α,β-Unsaturated Carbonyl Compounds

  • Baik, Woon-Phil;Yoon, Cheol-Hoon;Koo, Sang-Ho;Kim, Ha-Kwon;Kim, Ji-Han;Kim, Jeong-Ryul;Hong, Soo-Dong
    • Bulletin of the Korean Chemical Society
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    • v.25 no.4
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    • pp.491-500
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    • 2004
  • The Lewis acid-catalyzed reactions of anthrone with a variety of ethylenic substrates under various conditions have been studied. It has been observed that depending on kinds of ethylenic substrates and catalysts, products were varied. In particular, the $ZnCl_2$-catalyzed reaction of anthrone with ${\alpha},{\beta}$ -unsaturated ester gave bridged compounds 3 (Diels-Alder adduct type) and mono-Michael adduct 4 exclusively, while the base-catalyzed reaction gave 10,10-bis-Michael adduct as a major product independent of the amount of ethylenic substrate and base. Bridged compounds 3 were easily converted to the corresponding mono-Michael adduct 4 by a catalytic amount of base. Further Michael reaction of mono-Michael adducts with different ethylenic substrates in the presence of a catalytic amount of alkoxide gave unsymmetrical 10,10-bis Michael adducts in good or moderate yields.

Photochemistry of 1-(o-substituted -phenyl)-2-pentamethyldishilanyl Ethynes

  • Shim, Sang-Chul;Park, Seung-Ki
    • Journal of Photoscience
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    • v.6 no.1
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    • pp.13-19
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    • 1999
  • Irradiation of 1-(o-allyloxyphenyl)-2-pentamethyldisilanylenthyne 2a in methanol yields two 1 : 1 photoaddition products 3 and 4 via silacyclopropene intermediate. Photolysis of 2a with acetone in deaerated methylene chloride yields site specific and regioselective 1 : 1 adducts 6 ad 7 via silacyclopropene and 1-sila-1, 2-propdiene intermediate, respectively. Photolysis of 2a and 1-(o-(3', 3'-dimethyl-2'-propenylox)phenyl)-2-pen-tamethyldisilanylethyone 2b in benzene provides novel stereoselevtive intramolecular cyclization products 10 and 11, respectively. Irradiation of 1-(o-acetoxyphenyl)-2-pentamethyldisilanyl ethyne 2c in benzene yields the photo-Fries rearrangement products 18 and 19 and a photoproduct 17 via silacyclopropene intermediate. Photolysis of 1-(o-methoxycarbonlymethoxyphenyl)-2-pentamethyl disilanylenthyne 2d in benzene provides a novel intramolecular cycloaddition product 25 and 1-(o-methoxycarbonylemthoxiyphenyl)-2-trimethylsilylethyne 26 via silacyclopropene intermediate.

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