Preparation of primary and secondary alkyl phosphines from elemental phosphorus or phosphorus trichloride in organic solvents

A number of volatile and non-volatile primary and secondary alkyl phosphine s have been prepared by one-pot procedures from elemental phosphorus or fro m phosphorus trichloride. The element or chloride was first converted into trisodium phosphide by reaction with sodium in the presence of naphthalene or another solubilisation reagent. Subsequent addition of two equivalents o f t-butyl alcohol and an alkyl halide gave monoalkyl phosphines in fair to good yields. In situ conversion of the primary phosphine into a dialkyl pho sphine was achieved by metallation with BuLi or sodium and subsequent alkyl ation.