THE CHEMISTRY OF PERFLUOROALKANESULFONYL IODIDES

Article abstract of DOI:10.1016/S0022-1139(00)84369-9

The reaction between silver perfluoroalkanesulfinate (1) (R_F=a, Cl(CF2)6; b, Cl(CF2)4) and iodine in dichloromethane at low temperature (e. g. -30 deg C) resulted in the formation of the corresponding perfluoroalkanesulfonyl iodide(2), which was identified by its 19F NMR spectra.The perfluoroalkanesulfonyl iodide generated in situ reacted with various olefins to form two series of adducts, namely the normal adducts, R_FSO2CH2CHIR(3) and the adducts resulting from the loss of SO2, R_FCH2CHIR(4) in yields ranging from moderate to good.A radical reaction mechanism is proposed and tested by e.s.r. experiments.Perfluoroalkanesulfonyl iodide reacted with acetone and other compounds containing active hydrogen to give iodinated products.