Regioselective 1,3-dipolar cycloaddition and 1,2-addition between benzaldoxime NH-nitrone and perfluoro-2-methyl-2-pentene

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 19F NMR, and the absolute structure of perfluorinated adducts was confirmed by X-ray crystallography.