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http://dx.doi.org/10.5012/bkcs.2010.31.5.1172

Regioselective 1,3-Dipolar Cycloaddition and 1,2-Addition between Benzaldoxime NH-nitrone and Perfluoro-2-methyl-2-pentene  

Lee, Chan-Woo (Department of Chemistry, Hanyang University)
Park, Joo-Yuen (Department of Chemistry, University of Ulsan)
Kim, Hyun-Uk (Department of Chemistry, POSTECH)
Chi, Ki-Whan (Department of Chemistry, University of Ulsan)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.5, 2010 , pp. 1172-1176 More about this Journal
Abstract
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 $^{19}F$ NMR, and the absolute structure of perfluorinated adducts was confirmed by X-ray crystallography.
Keywords
NH-nitrone; Perfluorinated olefin; Cycloaddition; Regioselectivity;
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