Terrence Hogan and, Ayusman Sen
Mar 19, 1997
Citations
0
Influential Citations
28
Citations
Journal
Journal of the American Chemical Society
Abstract
Hydrogen peroxide and a trace of either ethene or propene initiated the conversion of ethane to propionic acid and its mixed anhydride (CH3CH2CO2H + CH3CH2COOCOCF3) and trifluoromethyl ethyl ketone, CH3CH2COCF3, by trifluoroacetic anhydride at 80 °C. For a fixed amount of H2O2, the amount of products formed increased with increasing amount of trifluoroacetic anhydride employed and was always higher than the amount of H2O2 added. These products were also obtained when H2O2 was replaced by other radical initiators: m-chloroperbenzoic acid, azobisisobutyronitrile, and PbEt4. With PbEt4, ethene or propene was not required for product formation and close to 500 equiv of products was formed for every equivalent of PbEt4 employed! Longer chain perfluorocarboxylic acid anhydrides reacted analogously; however, as the Rf group increased in length, a corresponding increase in mixed anhydride to ketone selectivity was observed. Methane gave very little product under the reaction conditions whereas propane underwent ...