the cold trap. The flask contents solidified on cooling. Three recrystallizations of the solid from benzene yielded diphenoxyphenyldifluorophosphorane (2.1 g, 33%) as a colorless crystalline solid, mp 68-70°.Phenoxydimethyldifluorophosphorane.-Dimethyltrifluorophosphorane (5.90 g, 0.050 mol) was added with stirring to phenyl trimethylsilyl ether (8.30 g, 0.050 mol) in an apparatus similar to that used in the previous experiment. The mixture was stirred under reflux for 6 hr and fluorotrimethylsilane (3.90 g, 81%) was collected in the cold trap. Distillation of the residue in vacuo yielded phenoxydimethyldifluorophosphorane (7.2 g, 75%), bp 72-74°(0.2 mm), as a colorless mobile liquid.A gray viscous residue (2.6 g) was left in the flask.Aryloxyphosphonium Hexafluorophosphates.-The following experiments illustrate the use of sodium fluoride in obtaining aryloxyphosphonium hexafluorophosphates in high yields from certain of the reactions we report.Tetraphenoxyphosphonium Hexafluorophosphate.-Phosphorus pentafluoride (5.0 g, 0.040 mol) was condensed onto a mixture of phenyl trimethylsilyl ether (13.2 g, 0.080 mol) and sodium fluoride (0.5 g) at liquid nitrogen temperature in a glass London, respectively.