AROMATIC POLYFLUORO-COMPOUNDS .46. NUCLEOPHILIC REPLACEMENT REACTIONS OF PENTAFLUOROPHENYLDIPHENYLPHOSPHINE AND ITS OXIDE AND SULPHIDE

Pentafluorophenyldiphenylphosphine (I) and its oxide (II) and sulphide (III) have been treated with sodium methoxide in methanol and with methylamine in both benzene and ethanol. All three reagents replaced only the para-fluorine substituent of the phosphine, but considerable ortho-replacement (82 and 46%, respectively, the remainder being para) in the oxide and sulphide occurred with methylamine in benzene; methylamine in ethanol gave only para-replacement. Sodium methoxide cleaved the pentafluorophenyl group completely from the oxide and partially from the sulphide.