REACTION OF UNSATURATED-COMPOUNDS WITH HYPOFLUOROUS ACID

The successful synthesis of hypofluorous acid by Studier and Appelman2 has prompted the study of the reactions of this novel molecule with organic substrates. Appelman and Bonnett have recently reported the hydroxylation of aromatic compounds3 by hypofluorous acid. The fact that hydroxylation rather than fluorination was observed in this system supports the hypothesis that HOF is polarized in the sense HOδ+-Fδ−. This unique polarization was initially suggested by NMR spectral data.4 Among the hypohalous acids, only HOF would be expected to be polarized in this way since all of the other halogen atoms are less electronegative than oxygen. 5 We would thus expect the Markownikoff addition of hypofluorous acid to alkenes to yield halohydrins of an orientation opposite to that resulting from the well-known Markownikoff addition of hypochlorous acid (HOδ+-CIδ+).6, 7 We have therefore decided to investigate the reaction of HOF with unsaturated molecules. © 1979, American Chemical Society. All rights reserved.