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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 6
BKCSDE 31(6)
June 20, 2010 

 
Title
Regio- and Diastereoselective 1,3-Dipolar Cycloaddition between Perfluoro-2-
methyl-2-pentene and Nitrones: A Facile Approach to Partially-Fluorinated
Isoxazolidines
Author
Mi Eun Moon, Joo Yeon Park, Eun Ha Jeong, Vaishali Vajpayee, Hyunuk Kim, Ki Whan Chi*
Keywords
Perfluorinated olefin, 1,3-Dipolar cycloaddition, Isoxazolidine derivatives
Abstract
Regio- and diastereoselective 1,3-dipolar cycloaddition reactions of nitrones {(Z)-α-phenyl-N-methylnitrone (1a) and (Z)-α-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 19F NMR, GC-MS and NOE measurements, and the absolute structure of 3a was confirmed by X-ray crystallography.
Page
1515 - 1518
Full Text
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