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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 5
BKCSDE 31(5)
May 20, 2010 

Regioselective 1,3-Dipolar Cycloaddition and 1,2-Addition between Benzaldoxime NH-nitrone and Perfluoro-2-methyl-2-pentene
Chan Woo Lee*, Joo Yuen Park, Hyunuk Kim, Ki Whan Chi*
NH-nitrone, Perfluorinated olefin, Cycloaddition, Regioselectivity
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 19F NMR, and the absolute structure of perfluorinated adducts was confirmed by X-ray crystallography.
1172 - 1176
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