This reaction was repeated to prepare O-diphenylphosphinyl hydroxylamine as this compound was reported to be a "less explosive" electrophilic aminating agent. Note: a recent improved preparation has been reported. (DSC measurements of the isolated compound showed that this is a high energy compound with a low onset temperature. Thus, no further work was done on this compound nor was it purified additionally.)
The solvent was changed to toluene rather than benzene.
A suspension of hydroxylamine in toluene was stirred vigorously at 5 C under nitrogen. Diphenylphosphinic chloride in toluene was added dropwise over 20 minutes, during which time solids separated. Stirring was continued for 30 minutes as the mixture warmed to rt. The solid was isolated by filtration and washed with cold water that was made slightly basic with 1M NaOH followed by washing with cold water. The solid was dried in a vac oven at rt over night. The solid was purified by recrystallization from MeOH. The DSC energy profile of the crude solid as well as the purified solid were similar. No further work was done with this material.