Bulletin of the Korean Chemical Society

  • 제31권6호
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  • Pages.1515-1518
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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

  • 투고 : 2009.06.23
  • 심사 : 2010.04.14
  • 발행 : 2010.06.20
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초록

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.

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참고문헌

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피인용 문헌

  1. 1,3-Dipolar Cycloadditions of Nitrones to Hetero-substituted Alkenes Part 2: Sila-, Thia-, Phospha- and Halo-substituted Alkenes vol.44, pp.1, 2012, https://doi.org/10.1080/00304948.2012.643193
  2. Efficient method for the synthesis of 1,2,3-triazole functionalized isoxazolidine derivatives by 1,3-dipolar cycloaddition of nitrones with terminal olefins vol.47, pp.5, 2017, https://doi.org/10.1080/00397911.2016.1271133
  3. ChemInform Abstract: Regio- and Diastereoselective 1,3-Dipolar Cycloaddition Between Perfluoro-2-methyl-2-pentene and Nitrones: A Facile Approach to Partially-Fluorinated Isoxazolidines. vol.41, pp.45, 2010, https://doi.org/10.1002/chin.201045124
  4. Regio- and stereoselective 1,3-dipolar cycloaddition reactions of C-aryl (or hetaryl)-N-phenylnitrones to monosubstituted ylidene malononitriles and 4-benzylidene-2-phenyloxazol-5(4H)-one vol.72, pp.5, 2017, https://doi.org/10.1515/znb-2016-0263