• Title/Summary/Keyword: Carbon-carbon bond formation

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Development of fluorination methodology for carbon-fluorine bond formation: old electrophilic fluorinating reagents

  • Bae, Dae Young;Lee, Eunsung
    • 대한방사성의약품학회지
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    • 제4권1호
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    • pp.11-15
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    • 2018
  • Electrophilic fluorinating reagents are typically efficient for carbon-fluorine (C-F) bonds formation due to their higher reactivity even under mild condition. Thus, they have been playing an important role to improve C-F bonds formation reactions via direct fluorination reaction with electrophilic fluorinating reagents or transition metal catalysis. Advances on the recent fluorination methods are mainly results of $Selectfluor^{TM}$'s capability on facile fluorination. In this mini-review, we describe synthesis and application of four old yet popular electrophilic fluorinating reagents such as N-fluorobenzenesulfonimide (NFSI), N-fluoropyridinium salts, $Selectfluor^{TM}$, and N-fluorosultam.

Pe-Co-Ni 분말 소결 금속과 탄소강의 이종재료간 레이저 용접부의 결함형성기구 연구 (A Study on the Formation Mechanism of Discontinuities in $CO_2$ Laser Fusion Zone of Fe-Co-Ni Sintered Segment and Carbon Steel)

  • 신민효;김태웅;박희동;이창희
    • Journal of Welding and Joining
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    • 제21권3호
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    • pp.58-67
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    • 2003
  • In this study, the formation mechanism of discontinuities in the laser fusion zone of diamond saw blade was investigated. $CO_2$ laser weldings were conducted along the butt between Fe base sintered tip and carbon steel shank with sets of variable welding parameters. The effect of heat input on irregular humps, outer cavity, inner cavity and bond strengh was evaluated. The optimum heat input to have a proper humps was in the range of 10.4~$17.6kJm_{-1}$. With increasing heat input, both outer and inner cavities were reduced. The outer cavity was caused by insufficient refill of keyhole, while inner cavity was caused by trapping of bubble in molten metal. The bubble came from sintered tip and intensive vaporization at bottom tip of the keyhole. A gas formation and low melting point element vaporization were not occurred during welding. We could not find any relationship between bond strength and amount of discontinuities. Because the fracture were occurred in not only sintered tip but also carbon steel shank due to hardness distributions.

Baylis-Hillman Reaction and Chemical Transformations of Baylis-Hillman Adducts

  • Lee, Ka-Young;Gowrisankar, Saravanan;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • 제26권10호
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    • pp.1481-1490
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    • 2005
  • Carbon-carbon single bond-forming reaction is the most useful and fundamental reaction in organic synthesis. Most of the basic carbon-carbon single bond-forming reactions, thus, developed in the past. In these respects, conceptually new C-C bond formation reaction can be highlighted. The Baylis-Hillman reaction was found at the early 1970’s. However, extensive studies on this highly potential reaction were started only before 15 years. This review has been written to shed more lights to the importance of Baylis-Hillman reaction. We have focused mainly on the reaction mechanism, conceptually related reactions, and chemical transformations of the Baylis-Hillman adducts.

Influence of Oxyfluorination on Properties of Polyacrylonitrile (PAN)- Based Carbon Fibers

  • Lim, In-Seub;Yoo, Seung-Hwa;Park, Il-Nam;Lee, Young-Seak
    • Carbon letters
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    • 제5권1호
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    • pp.12-17
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    • 2004
  • In this study, the oxyfluorination of PAN-based carbon fibers was undertaken at room temperature using fluorine-oxygen mixtures, and the influence of oxyfluorination on properties was investigated. The surface characteristics of the modified fiber were determined by using X-ray photoelectron spectroscopy (XPS) and dynamic contact angle analyzer. The oxyfluorination of carbon fibers was one of the more effective methods to increase surface wettability by the formation of semicovalent C-F bond and C-O bond depending on reaction conditions. When oxygen mole fraction is increased from 0.5 to 0.9, it is probable that attached fluorine atoms at the surface of the fibers reacted with other components. As increased oxyfluorination time and decreased its pressures, semi-covalent peak is increased at 0.5 of oxygen mole fraction. The total surface free energy of oxyfluorinated carbon fibers decreased with increasing oxygen mole fraction over 0.5. These results indicate that the surface of carbon fibers became much more hydrophilic after the short oxyfluorination. The surface free energy of oxyfluorinated carbon fibers progressively decreased after 10 min treatment. The polar components of surface free energies were however, significantly higher for all oxyfluorinated samples than that for the untreated carbon fiber.

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Transition metal-mediated/catalyzed fluorination methodology developed in the 2000s

  • Bae, Dae Young;Lee, Eunsung
    • 대한방사성의약품학회지
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    • 제3권2호
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    • pp.122-128
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    • 2017
  • In the 2000s, there has been a significant advance on carbon-fluorine (C-F) bond formation reactions via transition metal mediated or catalyzed methods. Of course, for the past 10 years, transition metal catalysis improves C-F bond formation in terms of practicality and even can be applied to C-18F bond formation reaction. In this mini-review, we summarize various transition metal mediated or catalyzed fluorination reactions, which were developed in the mid-2000s.

Development of fluorination methodology for carbon-fluorine bond formation: nucleophilic fluorinating reagents in the mid-2000s

  • Bae, Dae Young;Lee, Eunsung
    • 대한방사성의약품학회지
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    • 제3권2호
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    • pp.129-133
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    • 2017
  • Since carbon-fluorine (C-F) bonds play a key role to improve bioavailability and lipophilicity, they have found commonly in pharmaceuticals, radiopharmaceuticals, agrochemicals, and material science. Advances on the efficient method to introduce fluorine to complex organic molecules are mainly results of development of fluorination reagents and transition metal catalysts. In this mini-review, we want to emphasize two representative nucleophilic fluorinating reagents regarding carbon-fluorine bond formation, which were developed in the mid-2000s.

Theoretical Studies Gas Phase Reaction of Alkoxide-Exchange at Silicon and Carbon Centers$^\dag$

  • Lee, Ik-Choon;Yang, Ki-Yull;Park, Byong-Seo;Lee, Kae-Soo
    • Bulletin of the Korean Chemical Society
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    • 제7권3호
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    • pp.231-235
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    • 1986
  • MNDO and ab initio calculations for gas phase reactions of alkoxide-exchange at silicon and carbon centers have been performed. Results show that MNDO values of ${\Delta}$E's of these reactions closely parallel those of the STO-3G method. The alkoxide-exchange at silicon is shown to be facile due to the formation of stable five-coordinate intermediate while the reaction at carbon is predicted to proceed with high barrier; the difference in this substitution behavior between carbon and silicon is shown to be due to an easy valence shell expansion of silicon in accommodating an extra bond in the formation of stable five-coordinate intermediates.